Issue 23, 2018

Biomimetic syntheses of C23 terpenoids: structural revision of salyunnanin A and confirmation of hassanane

Abstract

Salyunnanin A and hassanane, two C23 terpenoids, were achieved from (+)-carnosic acid in 6 and 5 steps, respectively. The synthetic strategy was primarily inspired by the biogenetic hypothesis and provided access to the natural products via elimination, double Michael-type addition in one pot to prepare the corresponding 6,20-epoxyabietanes, and bismuthonium ylide induced ring expansion of o-quinone to construct 2-acyl-3-hydroxytropone.

Graphical abstract: Biomimetic syntheses of C23 terpenoids: structural revision of salyunnanin A and confirmation of hassanane

Supplementary files

Article information

Article type
Research Article
Submitted
26 Jul 2018
Accepted
25 Oct 2018
First published
25 Oct 2018

Org. Chem. Front., 2018,5, 3469-3475

Biomimetic syntheses of C23 terpenoids: structural revision of salyunnanin A and confirmation of hassanane

X. Zhang, Z. Li, H. Yong and Z. Xie, Org. Chem. Front., 2018, 5, 3469 DOI: 10.1039/C8QO00772A

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