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Divergent Biomimetic Total Syntheses of Ganocins A–C, Ganocochlearins C and D, and Cochlearol T.
- Source :
-
Angewandte Chemie . 5/4/2020, Vol. 132 Issue 19, p7489-7494. 6p. - Publication Year :
- 2020
-
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. [ABSTRACT FROM AUTHOR]
- Subjects :
- *BIOMIMETIC synthesis
*CHEMICAL synthesis
*CHEMICAL elements
*GANODERMA
*PHENOL
Subjects
Details
- Language :
- English
- ISSN :
- 00448249
- Volume :
- 132
- Issue :
- 19
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie
- Publication Type :
- Academic Journal
- Accession number :
- 142847648
- Full Text :
- https://doi.org/10.1002/ange.202000677