4.7 Article

1,2-Metallate Rearrangement as a Toolbox for the Synthesis of Allylic Alcohols

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Article Chemistry, Multidisciplinary

Sparteine-Free, Highly Stereoselective Construction of Complex Allylic Alcohols Using 1,2-Metallate Rearrangements

Yannick Linne et al.

Summary: Stereotriads bearing allylic alcohols are important structures in natural products, and finding new stereoselective methods to access them is highly desired. We discovered that using chiral polyketide fragments allows for the efficient Hoppe-Matteson-Aggarwal rearrangement without the need for sparteine, resulting in high yields and diastereoselectivities. This protocol provides a valuable alternative to the Nozaki-Hiyama-Takai-Kishi reaction. The reversal of stereochemical outcome upon switching directing groups can be explained by conformational analysis and a Felkin-like model at the density functional theory level.

JACS AU (2023)

Article Chemistry, Organic

Total Syntheses of Strasseriolide A and B, Antimalarial Macrolide Natural Products

Leah J. Salituro et al.

Summary: This study reports the first total syntheses of strasseriolide A and B. Strasseriolide B exhibits potent activity against the wild-type malaria parasite Plasmodium falciparum and good activity against a chloroquine-resistant strain. A convergent strategy was employed, utilizing an aldehyde-acid fragment and a vinyl iodide-alcohol fragment, both prepared from chiral pool starting materials. The fragments were combined through a Yamaguchi esterification and cyclized with a Nozaki-Hiyama-Kishi reaction, resulting in the assembly of strasseriolide B in a 16-step LLS.

ORGANIC LETTERS (2022)

Article Chemistry, Multidisciplinary

The Total Synthesis of Chondrochloren A

Yannick Linne et al.

Summary: The first total synthesis of chondrochloren A was achieved using a 1,2-metallate rearrangement addition as an alternative to the Nozaki-Hiyama-Kishi reaction. This approach not only overcomes the challenges of the polyketide segment but also provides a novel strategy for assembling polyketidal frameworks, utilizing a Z-selective cross coupling to form the Z-enamide.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Organic

Synthesis of the C18-C27 Fragment of Georatusin

Yannick Linne et al.

Summary: The researchers proposed a bidirectional approach for the rapid construction of highly reduced polyketide fragments for the synthesis of georatusin.

ARKIVOC (2021)

Article Chemistry, Multidisciplinary

Desymmetrization of C2-Symmetric Bis(Boronic Esters) by Zweifel Olefinations

Yannick Linne et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

Article Chemistry, Multidisciplinary

Stereospecific Allylic Functionalization: The Reactions of Allylboronate Complexes with Electrophiles

Cristina Garcia-Ruiz et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Multidisciplinary

Enantioselective Conjunctive Cross-Coupling of Bis(alkenyl)borates: A General Synthesis of Chiral Allylboron Reagents

Emma K. Edelstein et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Multidisciplinary

Selective uni- and bidirectional homologation of diborylmethane

Daniel J. Blair et al.

CHEMICAL SCIENCE (2017)

Review Chemistry, Multidisciplinary

Role of the Nozaki-Hiyama-Takai-Kishi Reaction in the Synthesis of Natural Products

Alejandro Gil et al.

CHEMICAL REVIEWS (2017)

Article Chemistry, Multidisciplinary

Regio- and Stereoselective Homologation of 1,2-Bis(Boronic Esters): Stereocontrolled Synthesis of 1,3-Diols and Sch725674

Alexander Fawcett et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Review Chemistry, Multidisciplinary

Lithiation-Borylation Methodology and Its Application in Synthesis

Daniele Leonori et al.

ACCOUNTS OF CHEMICAL RESEARCH (2014)

Review Chemistry, Multidisciplinary

Catalytic Asymmetric Synthesis of Allylic Alcohols and Derivatives and their Applications in Organic Synthesis

Alexandre Lumbroso et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Article Chemistry, Organic

Design, Synthesis, and Biological Evaluations of Aplyronine A-Mycalolide B Hybrid Compound

Kenichi Kobayashi et al.

ORGANIC LETTERS (2012)

Article Chemistry, Multidisciplinary

Use of alkyl 2,4,6-triisopropylbenzoates in the asymmetric homologation of challenging boronic esters

Robin Larouche-Gauthier et al.

CHEMICAL COMMUNICATIONS (2011)

Article Chemistry, Organic

Total Syntheses of Rhodiolosides A and D and of Sachalinols A-C

Kristina Simon et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2011)

Article Chemistry, Multidisciplinary

Total Synthesis of the Spirocyclic Imine Marine Toxin (-)-Gymnodimine and an Unnatural C4-Epimer

Ke Kong et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

Article Plant Sciences

Monoamine oxidase inhibition by Rhodiola rosea L. roots

Daphne van Diermen et al.

JOURNAL OF ETHNOPHARMACOLOGY (2009)

Article Chemistry, Medicinal

Revised absolute stereochemistry of rhodiolosides A-D, rhodiolol A and sachalinol A from Rhodiola rosea

Wei Li et al.

CHEMICAL & PHARMACEUTICAL BULLETIN (2008)

Article Multidisciplinary Sciences

Enantiodivergent conversion of chiral secondary alcohols into tertiary alcohols

Jake L. Stymiest et al.

NATURE (2008)

Article Plant Sciences

Phenylalkanoids and monoterpene analogues from the roots of Rhodiola rosea

Zulfiqar Ali et al.

PLANTA MEDICA (2008)

Article Chemistry, Organic

Synthesis and stereochemistry of (-)-rosiridol and (-)-rosiridin

Elisabeth Schoettner et al.

TETRAHEDRON LETTERS (2008)

Article Chemistry, Medicinal

Rhodiolosides A-E, monoterpene glycosides from Rhodiola rosea

Guizhi Ma et al.

CHEMICAL & PHARMACEUTICAL BULLETIN (2006)

Article Chemistry, Medicinal

Prolyl endopeptidase inhibitors from the underground part of Rhodiola sachalinensis

WZ Fan et al.

CHEMICAL & PHARMACEUTICAL BULLETIN (2001)

Review Chemistry, Multidisciplinary

Catalytic asymmetric organozinc additions to carbonyl compounds

L Pu et al.

CHEMICAL REVIEWS (2001)