4.6 Review

Recent advances in the syntheses of guaianolides

Related references

Note: Only part of the references are listed.
Article Chemistry, Applied

Chemical constituents from Centaurothamnus maximus and their antimicrobial activity

Muneera S. M. Al-Saleem et al.

Summary: A new sesquiterpene lactone, along with twenty-one known compounds, were identified from the aerial parts of Centaurothamnus maximus. The isolated compounds showed promising antibacterial and antifungal activities.

NATURAL PRODUCT RESEARCH (2023)

Article Plant Sciences

Two new guaianolide-type sesquiterpenoids with NO inhibitory activity from Chrysanthemum indicum

Jin-Feng Xue et al.

Summary: Two new guaianolide-type sesquiterpenoids and six known analogues were isolated from Chrysanthemum indicum. The structures of the new compounds were determined through extensive spectroscopic analysis. The compounds showed inhibitory activity on nitric oxide production.

JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH (2023)

Article Chemistry, Multidisciplinary

Semisynthesis of (-)-Bufospirostenin A Enabled by Photosantonin Rearrangement Reaction

Jun Huang et al.

Summary: The article describes an enantioselective semisynthesis of (-)-bufospirostenin A, involving the use of biomimetic and diastereoselective reactions for construction of the bicyclic motif, and a Co-catalyzed reversible double-bond isomerization reaction for installing the double bond.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Organic

Total Syntheses of Proposed Structures of 4,10-Dihydroxy-8,12-guaianolides

Yuki Kimura et al.

Summary: The total syntheses of two natural products, 4,10-dihydroxy-8,12-guaianolides, were achieved. The construction of the typical 5,7-fused system of 8,12-guaianolides using a ring expansion reaction revealed that the previously reported structures of both natural products were incorrect.

ORGANIC LETTERS (2022)

Article Plant Sciences

A Dimerosesquiterpene and Sesquiterpene Lactones from Artemisia argyi Inhibiting Oncogenic PI3K/AKT Signaling in Melanoma Cells

Lara Durr et al.

Summary: A screening of over 2500 plant extracts in melanoma cells revealed that the ethyl acetate extract from Artemisia argyi displayed significant inhibition of the PI3K/AKT pathway. Through activity profiling, 21 active compounds were isolated, including one novel dimerosequiterpenoid, one new disesquiterpenoid, three new guaianolides, 12 known sesquiterpenoids, and four known flavonoids.

JOURNAL OF NATURAL PRODUCTS (2022)

Article Chemistry, Organic

Asymmetric Total Synthesis of Eupalinilide E, a Promoter of Human HSPC Expansion

Ramkrishna Maity et al.

Summary: A concise and scalable asymmetric total synthesis of eupalinilde E, starting from (R)-(???)-carvone, is reported in this article. The synthesis involves 12 steps and achieves an overall yield of 20%. Key steps include a tandem Favorskii rearrangement???elimination reaction for the chromatography-free synthesis of carvone-derived 2-cyclopentene carbaldehyde, and a catalyst-free stereospecific tandem allylboration???lactonization using recyclable trifluoroethanol as a promoter and solvent, leading to the formation of ??-hydroxymethyl-??methylene-??-butyrolactone.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Diastereoselective Allylation in the Divergent Total Syntheses of Guaianolides (+)-Ligustrin and (+)-Grosheimin and the Formal Synthesis of (-)-Eupalinilide E

Gujjula V. Ramakrishna et al.

Summary: In this study, an efficient diastereoselective allylation of aldehydes with functionalized allyl bromolactone was utilized to achieve the protecting-group-free divergent total synthesis of various guaianolides (+)-ligustrin, (+)-8-epi-ligustrin, and (+)-grosheimin, as well as the formal synthesis of (-)-eupalinilide E.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Organic

Biomimetic Synthesis of Lavandiolides H, I, and K and Artematrolide F via Diels-Alder Reaction

Tian-Ze Li et al.

Summary: The biomimetic synthesis from arglabin led to the successful production of guaianolide dimers, trimers, and tetramers, with the trimer showing stronger anti-hepatoma cytotoxicity than sorafenib.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Total Syntheses of Paraconic Acids and 1,10-seco-Guaianolides via a Barbier Allylation/Translactonization Cascade of 3-(Bromomethyl)-2(5H)-furanone

Weilong Liu et al.

Summary: A palladium-catalyzed Barbier allylation/translactonization cascade reaction was developed for the rapid construction of a key motif in sesquiterpenes, showing a broad substrate scope and enabling the synthesis of two paraconic acids and two 1,10-seco-guaianolides in a protecting-group-free total synthesis approach.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Enantioselective Total Synthesis of the Guaianolide (-)-Dehydrocostus Lactone by Enediyne Metathesis

Felix Kaden et al.

Summary: In this study, the hydroazulene core of a bioactive sesquiterpenoid was generated by domino enediyne metathesis, with three out of four stereogenic centers of the target installed in a single step through a triple hydroboration/oxidation reaction. The enantiopure acyclic metathesis substrate was easily obtained via an asymmetric anti aldol reaction, and late-stage double carbonyl olefination was efficiently carried out after masking the gamma-lactone as an acetal.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Asymmetric Total Synthesis of (-)-Dehydrocostus Lactone by Domino Metathesis

Felix Kaden et al.

Summary: An efficient total synthesis of (-)-dehydrocostus lactone was achieved through a multi-step approach involving stereoselective reactions, hydroboration/oxidation, and olefination, significantly improving the efficiency of the synthesis process.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Review Chemistry, Multidisciplinary

Application of Pauson-Khand reaction in the total synthesis of terpenes

Majid M. Heravi et al.

Summary: The Pauson-Khand reaction (PKR) is a key cycloaddition reaction that can efficiently synthesize cyclopentenones and their derivatives in a single step, making it a popular method in the total synthesis of terpenes.

RSC ADVANCES (2021)

Article Chemistry, Organic

Total synthesis of cynaropicrin

Tenma Nakamura et al.

Summary: Cynaropicrin, a sesquiterpene lactone found in artichoke, has diverse biological activities and was successfully synthesized from (S)-alpha-pinene through a series of reactions including stereoselective Favorskii rearrangement and indium-promoted diastereoselective Barbier reaction.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Article Plant Sciences

Preparation and Phytotoxicity Evaluation of 11,13-Dehydro seco-Guaianolides

Nuria Chinchilla et al.

JOURNAL OF NATURAL PRODUCTS (2019)

Article Chemistry, Multidisciplinary

Allylative Approaches to the Synthesis of Complex Guaianolide Sesquiterpenes from Apiaceae and Asteraceae

Xirui Hu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Medicinal

Divergent synthesis of thapsigargin analogs

Hang Chu et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2018)

Article Chemistry, Medicinal

Natural Product Micheliolide (MCL) Irreversibly Activates Pyruvate Kinase M2 and Suppresses Leukemia

Jing Li et al.

JOURNAL OF MEDICINAL CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

Scalable Synthesis of (-)-Thapsigargin

Hang Chu et al.

ACS CENTRAL SCIENCE (2017)

Article Chemistry, Multidisciplinary

A Concise, Efficient and Scalable Total Synthesis of Thapsigargin and Nortrilobolide from (R)-(-)-Carvone

Dezhi Chen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Organic

Unified total synthesis of (+)-chinensiolide B and (+)-8-epigrosheimin

Saumen Hajra et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

Total Synthesis of (+)-Chinensiolide B from -Santonin

Lingqiong Zhang et al.

CHINESE JOURNAL OF CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

A Double Allylation Strategy for Gram-Scale Guaianolide Production: Total Synthesis of (+)-Mikanokryptin

Xirui Hu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Total Synthesis of (±)-Integrifolin

Katsuya Shimomaki et al.

CHEMISTRY-A EUROPEAN JOURNAL (2016)

Review Plant Sciences

Sesquiterpene Lactones: More Than Protective Plant Compounds With High Toxicity

Guillermo Federico Padilla-Gonzalez et al.

CRITICAL REVIEWS IN PLANT SCIENCES (2016)

Article Chemistry, Multidisciplinary

Synthesis of Eupalinilide E, a Promoter of Human Hematopoietic Stem and Progenitor Cell Expansion

Trevor C. Johnson et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Organic

Enantioselective Synthesis of Guaianolides in the Osmitopsin Family by Domino Metathesis

Andre Barthel et al.

ORGANIC LETTERS (2016)

Review Biochemistry & Molecular Biology

Arglabin: From isolation to antitumor evaluation

Shabir H. Lone et al.

CHEMICO-BIOLOGICAL INTERACTIONS (2015)

Review Chemistry, Organic

Trends in the Synthesis and Functionalization of Guaianolides

Alejandro Santana et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2015)

Article Chemistry, Organic

Concise synthesis of thapsigargin from nortrilobolide

Francois Crestey et al.

TETRAHEDRON LETTERS (2015)

Article Chemistry, Organic

Hemisynthesis of a naturally occurring clinically significant antitumor arglabin from ludartin

Shabir H. Lone et al.

TETRAHEDRON LETTERS (2015)

Article Chemistry, Organic

Acyloxylation of Cyclic Enones: Synthesis of Densely Oxygenated Guaianolides

Ruben Marin-Barrios et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

Review Chemistry, Organic

Sonogashira coupling in natural product synthesis

Dan Wang et al.

ORGANIC CHEMISTRY FRONTIERS (2014)

Article Chemistry, Multidisciplinary

Total Syntheses of Ainsliadimer B and Gochnatiolides A and B

Dongliang Xia et al.

CHEMISTRY-A EUROPEAN JOURNAL (2013)

Review Toxicology

Sesquiterpene lactones: Adverse health effects and toxicity mechanisms

M. Helena R. Amorim et al.

CRITICAL REVIEWS IN TOXICOLOGY (2013)

Article Chemistry, Organic

Improved synthesis of (R)-7-hydroxycarvone from (S)-α-pinene

Yuki Egoshi et al.

TETRAHEDRON LETTERS (2013)

Review Oncology

Sesquiterpene lactones as drugs with multiple targets in cancer treatment: focus on parthenolide

Maria Regina Orofino Kreuger et al.

ANTI-CANCER DRUGS (2012)

Article Chemistry, Organic

Biomimetic Semisynthesis of Arglabin from Parthenolide

Jia-Dai Zhai et al.

JOURNAL OF ORGANIC CHEMISTRY (2012)

Article Chemistry, Multidisciplinary

Biomimetic Syntheses of (-)-Gochnatiolides A-C and (-)-Ainsliadimer B

Chao Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Article Chemistry, Organic

Concise Total Synthesis of (-)-8-Epigrosheimin

Haishen Yang et al.

ORGANIC LETTERS (2011)

Article Chemistry, Multidisciplinary

Total Synthesis of (+)-Chinensiolide B via Tandem Allylboration/Lactonization

Tim G. Elford et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Article Chemistry, Organic

A Biomimetic Total Synthesis of (+)-Ainsliadimer A

Chao Li et al.

ORGANIC LETTERS (2010)

Article Chemistry, Multidisciplinary

Ionic and Organometallic Reductions with N-Heterocyclic Carbene Boranes

Qianli Chu et al.

CHEMISTRY-A EUROPEAN JOURNAL (2009)

Article Plant Sciences

Guaianolides in apiaceae: perspectives on pharmacology and biosynthesis

Damian Paul Drew et al.

PHYTOCHEMISTRY REVIEWS (2009)

Article Chemistry, Organic

Diastereoselective total synthesis of 8-epigrosheimin

Haishen Yang et al.

TETRAHEDRON LETTERS (2009)

Review Chemistry, Organic

Synthesis of biologically active guaianolides with a trans-annulated lactone moiety

Andreas Schall et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2008)

Article Chemistry, Organic

(BDP)CuH: A hot Stryker's reagent for use in achiral conjugate reductions

Benjamin A. Baker et al.

ORGANIC LETTERS (2008)

Article Biochemistry & Molecular Biology

Quantitative structure-activity relationship of sesquiterpene lactones with cytotoxic activity

Marcus T. Scotti et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2007)

Article Chemistry, Multidisciplinary

Pd-catalyzed borylative cyclization of 1,6-enynes

Juan Marco-Martinez et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

Article Chemistry, Organic

Total synthesis of thapsigargin, a potent SERCA pump inhibitor

Matthew Ball et al.

ORGANIC LETTERS (2007)

Article Chemistry, Multidisciplinary

Enantioselective synthesis of arglabin

Srinivas Kalidindi et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2007)

Review Chemistry, Medicinal

Naturally occurring NF-κB inhibitors

Nguyen-Hai Nam

MINI-REVIEWS IN MEDICINAL CHEMISTRY (2006)

Article Chemistry, Applied

A simple modification to prevent side reactions in Swern-type oxidations using Py-SO3

LJ Chen et al.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2006)

Article Chemistry, Organic

Facile synthesis of 2-alkynyl buta-1,3-dienes via sonogashira cross-coupling methodology

LX Shao et al.

JOURNAL OF ORGANIC CHEMISTRY (2005)

Article Agriculture, Multidisciplinary

Application of Hansch's model to guaianolide ester derivatives:: A quantitative structure-activity relationship study

FA Macías et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2005)

Article Chemistry, Organic

Oxidation of carbon-silicon bonds: The dramatic advantage of strained siletanes

JD Sunderhaus et al.

ORGANIC LETTERS (2003)

Article Chemistry, Multidisciplinary

A general and efficient copper catalyst for the amidation of aryl halides

A Klapars et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002)

Article Chemistry, Multidisciplinary

Pd-catalyzed intermolecular amidation of aryl halides: The discovery that xantphos can be trans-chelating in a palladium complex

JJ Yin et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002)

Article Chemistry, Organic

Synthesis of alpha-alkylidene-beta-ethoxycarbonyl cyclopentanones and -gamma-butyrolactones

F Beji et al.

SYNTHETIC COMMUNICATIONS (2000)