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Divergent Biomimetic Total Syntheses of Ganocins A–C, Ganocochlearins C and D, and Cochlearol T by Hui Shao; Xiaonan Gao; Zhong‐Tian Wang; Ziwei Gao; Yu‐Ming Zhao is a Chemistry article available to read on EtoBox.

What is Divergent Biomimetic Total Syntheses of Ganocins A–C, Ganocochlearins C and D, and Cochlearol T about?

## Abstract A divergent synthetic approach to six Ganoderma meroterpenoids, namely ganocins A–C, ganocochlearins C and D, and cochlearol T, has been developed for the first time. This synthetic route features a two‐phase strategy which includes early‐stage rapid construction of a common planar tricyclic intermediate followed by highly selective late‐stage transformations into various Ganoderma meroterpenoids. Key to the strategy are a bioinspired intramolecular hetero‐Diels–Alder reaction and Stahl‐type oxidative aromatization, allowing efficient formation of the common tricyclic phenol intermediate. A nucleophilic dearomatization of the phenol unit, combined with a regioselective 1,4‐reduction of the resulting dienone, enabled rapid access to ganocins B and C. Additionally, site‐selective Mukaiyama hydration, followed by an intramolecular oxa‐Michael addition/triflation cascade, served as a key strategic element in the chemical synthesis of ganocin A.

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Author

Hui Shao; Xiaonan Gao; Zhong‐Tian Wang; Ziwei Gao; Yu‐Ming Zhao

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley; Research Square (ISSN 0044-8249)

Published

2020

Language

EN

Field

Chemistry (Physical Sciences)