4.8 Article

Divergent total synthesis of the revised structures of marine anti-cancer meroterpenoids (+)-dysiherbols A-E

Related references

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

Construction of the Tetracyclic Core Structure of Dysiherbols A-C

Rong Liu et al.

Summary: This study presents a synthetic approach to the tetracyclic core structure of Dysiherbols A-C. The synthesis involves the intramolecular [2 + 2] cycloaddition to introduce a fused 6/4 ring system, followed by a Pd-catalyzed semipinacol rearrangement/C-sp2-H arylation cascade to construct ring C, and a visible-light-mediated ring-opening of cyclopropyl silyl ether to install the tetracyclic core of Dysiherbols.

ORGANIC LETTERS (2022)

Article Chemistry, Multidisciplinary

Enantioselective Total Synthesis of Dysiherbols A, C, and D

Shengkun Hu et al.

Summary: This paper reports the enantioselective total synthesis of dysiherbols A, C, and D using a photo-induced quinone-alkene [2 + 2] cycloaddition and a tandem [1,2]-anionic rearrangement/cyclopropane fragmentation as key elements. The originally proposed structures of dysiherbols C and D were revised based on the synthesis. Computational studies revealed insights into the unprecedented [1,2]-anionic rearrangement.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Multidisciplinary

Asymmetric Total Synthesis of Taxol

Ya-Jian Hu et al.

Summary: Taxol is a famous natural diterpenoid and important anticancer medicine with synthetic challenges. This study presents an asymmetric total synthesis of Taxol through a concise approach and the efficient construction of the challenging eight-membered ring. The new convergent approach allows for the creation of Taxol derivatives for further biological research.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Organic

Magnesium Monoperphthalate (MMPP): a Convenient Oxidant for the Direct Rubottom Oxidation of Malonates, β-Keto Esters, and Amides

Sara Meninno et al.

Summary: A mild and convenient protocol using cheap and stable magnesium monoperphthalate (MMPP) as the oxidant was developed for the alpha-hydroxylation of alpha-substituted malonates, beta-ketoesters, and beta-ketoamides. The protocol allows for the synthesis of various compounds in good yields at room temperature.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Enantioselective Total Synthesis and Structural Revision of Dysiherbol A

Julian Baars et al.

Summary: A 12-step total synthesis of the natural product dysiherbol A was achieved, revealing the need for revision of the originally proposed structure and absolute configuration. The synthesis involved key steps including Cu-catalyzed addition/enolate-trapping, Au-catalyzed double cyclization, and late installation of the C5-bridgehead methyl group. Spectroscopic measurements confirmed the identity of the synthetic compound with the natural product but with an opposite molecular rotation.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Total Synthesis of Anti-Cancer Meroterpenoids Dysideanone B and Dysiherbol A and Structural Reassignment of Dysiherbol A

Chuanke Chong et al.

Summary: The first total synthesis of marine anti-cancer meroterpenoids dysideanone B and dysiherbol A was accomplished using a divergent approach. Key features include site and stereoselective alpha-position alkylation, intramolecular radical cyclization, and intramolecular Heck reaction. Additionally, it was found that the ethoxy group in dysideanone B may originate from the solvent ethanol.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Organic

Recent advances in the total synthesis of natural products bearing the contiguous all-carbon quaternary stereocenters

Zhengyuan Xin et al.

Summary: This paper focuses on the importance of contiguous all-carbon quaternary centers in natural products and recent synthetic strategies used in total syntheses. By reviewing 12 representative synthetic examples, the power of these reactions in constructing such centers is showcased to inspire future exploration.

TETRAHEDRON LETTERS (2021)

Article Chemistry, Organic

Bioinspired Total Synthesis of Marine Anticancer Meroterpenoids Dysideanone B and Dysiherbol A and Structure Revision of Dysiherbol A

Chuanke Chong et al.

Summary: This paper briefly highlights recent progress on the total synthesis of marine anticancer sesquiterpene quinone/hydroquinone dysideanone B and dysiherbol A, detailing key transformations in constructing the core structures of both compounds and revealing the possible origin of an ethoxy group in dysideanone B. The structure of dysiherbol A was also revised through total synthesis. Schmalz's synthesis of dysiherbol A was included in this study.

SYNLETT (2021)

Article Chemistry, Multidisciplinary

Scalable Total Synthesis of (-)-Vinigrol

Xuerong Yu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Reductive Heck Reaction: An Emerging Alternative in Natural Product Synthesis

Tapas Ghosh

CHEMISTRYSELECT (2019)

Article Chemistry, Multidisciplinary

Asymmetric Total Synthesis of (-)-Vinigrol

Long Min et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Review Chemistry, Medicinal

Bioactive Prenyl- and Terpenyl-Quinones/Hydroquinones of Marine Origin

Pablo A. Garcia et al.

MARINE DRUGS (2018)

Review Chemistry, Multidisciplinary

Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms

Martin Bueschleb et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Nitrosopurines En Route to Potently Cytotoxic Asmarines

Kanny K. Wan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Review Chemistry, Organic

Allylic Oxidations in Natural Product Synthesis

Akihiko Nakamura et al.

SYNTHESIS-STUTTGART (2013)

Article Chemistry, Organic

Synthesis of (-)-callicarpenal, a potent arthropod repellent

Taotao Ling et al.

TETRAHEDRON (2011)

Article Chemistry, Organic

Quinone/Hydroquinone Sesquiterpenes

I. S. Marcos et al.

MINI-REVIEWS IN ORGANIC CHEMISTRY (2010)

Review Chemistry, Medicinal

Cytotoxic Terpene Quinones from Marine Sponges

Marina Gordaliza

MARINE DRUGS (2010)

Review Chemistry, Multidisciplinary

Palladium-catalyzed cross-coupling reactions in total synthesis

KC Nicolaou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2005)

Review Chemistry, Multidisciplinary

The asymmetric intramolecular Heck reaction in natural product total synthesis

AB Dounay et al.

CHEMICAL REVIEWS (2003)

Article Chemistry, Multidisciplinary

Total synthesis of ecteinascidin 743

A Endo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002)

Article Chemistry, Multidisciplinary

Total synthesis of asperazine

SP Govek et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001)

Article Chemistry, Multidisciplinary

Intramolecular nucleophilic addition of aryl bromides to ketones catalyzed by palladium

LG Quan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2000)