Total Synthesis of Asperchalasines A, D, E, and H

The first total syntheses of the cytochalasan dimers asperchalasines A, D, E, and H have been accomplished. The key steps of the synthesis include a highly stereoselective intermolecular Diels–Alder reaction and a Horner–Wadsworth–Emmons macrocyclization to establish the key monomer aspochalasin B,...

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Published inAngewandte Chemie International Edition Vol. 57; no. 43; pp. 14221 - 14224
Main Authors Long, Xianwen, Ding, Yiming, Deng, Jun
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 22.10.2018
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Biological properties
biomimetic synthesis
Biomimetics
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Cyclization
Cycloaddition
Cycloaddition Reaction
Cytochalasins - chemical synthesis
Cytochalasins - chemistry
Dimers
natural products
Oxidation-Reduction
Physical Sciences
Science & Technology
Stereoselectivity
total synthesis
dimers
ASPERGILLUS-FLAVIPES QCS12
ISOINDOLONE NUCLEUS
RING-SYSTEM
natural products
cycloaddition
PROXIPHOMIN
DIELS-ALDER REACTION
CYTOCHALASAN SYNTHESIS
CHAETOGLOBOSIN
total synthesis
LITHIUM
biomimetic synthesis
MEROCYTOCHALASANS
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Summary:The first total syntheses of the cytochalasan dimers asperchalasines A, D, E, and H have been accomplished. The key steps of the synthesis include a highly stereoselective intermolecular Diels–Alder reaction and a Horner–Wadsworth–Emmons macrocyclization to establish the key monomer aspochalasin B, and an intermolecular Diels–Alder reaction followed by a biomimetic oxidative heterodimerization by 5+2 cycloaddition to furnish asperchalasine A. The synthetic efforts provide insight into the biosynthetic pathway of cytochalasan dimers and enables the further study of their biological properties. Making two into one: Total syntheses of asperchalasines A, D, E, and H are reported. The key steps of the synthesis include an intermolecular Diels–Alder (DA) reaction and a Horner–Wadsworth–Emmons macrocyclization to establish the key monomer aspochalasin B, and an intermolecular DA reaction followed by a biomimetic oxidative heterodimerization to furnish asperchalasine A. This synthesis provides insight into the biosynthetic pathway of cytochalasan dimers.
Bibliography:These authors contributed equally to this work.
Dedicated to the 80th anniversary of the Kunming Institute of Botany, Chinese Academy of Sciences
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201808481