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

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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

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Publication details

The article was received on 26 Jul 2018, accepted on 25 Oct 2018 and first published on 25 Oct 2018


Article type: Research Article
DOI: 10.1039/C8QO00772A
Citation: Org. Chem. Front., 2018, Advance Article
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    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, Advance Article , DOI: 10.1039/C8QO00772A

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