A Universal Strategy for Synthesis of Agropyrenol Family. Total Synthesis of Agropyrenol, Sordarial, and Heterocornol A and B.
J Org Chem
; 87(23): 15947-15962, 2022 12 02.
Article
em En
| MEDLINE
| ID: mdl-36378998
ABSTRACT
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.
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Ano de publicação:
2022
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Article