A Universal Strategy for Synthesis of Agropyrenol Family. Total Synthesis of Agropyrenol, Sordarial, and Heterocornol A and B

A divergent strategy for natural polyketides synthesis has been designed. This synthetic route allowed chemical alterations leading to all stereoisomers of the natural agropyrenol 1, sordarial 2, and heterocornol B 4. Key steps involve desymmetrization of divinylcarbinol using asymmetric Sharpless e...

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Published inJournal of organic chemistry Vol. 87; no. 23; pp. 15947 - 15962
Main Authors Markovič, Martin, Koóš, Peter, Sokoliová, Saskia, Boháčiková, Nikola, Vyskočil, Tomáš, Moncoľ, Ján, Gracza, Tibor
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.12.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Naphthalenes
Physical Sciences
Science & Technology
Stereoisomerism
ASYMMETRIC-SYNTHESIS
DERIVATIVES
HEXAKETIDES
CONFIGURATION
CONSTITUENTS
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Summary:A divergent strategy for natural polyketides synthesis has been designed. This synthetic route allowed chemical alterations leading to all stereoisomers of the natural agropyrenol 1, sordarial 2, and heterocornol B 4. Key steps involve desymmetrization of divinylcarbinol using asymmetric Sharpless epoxidation and Heck coupling of an easily available aromatic partner and prepared chiral alkene. The versatility of the synthetic method was demonstrated on the preparation of heterocornol A 3 and sordariol 5. The absolute and relative configurations of prepared natural compounds 2·1/3C6H12 and 4 were confirmed and assigned by single-crystal X-ray analysis.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02092