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Issue 12, 2017
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Bioinspired synthesis of pentacyclic onocerane triterpenoids

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Abstract

The first chemical synthesis of pentacyclic onocerane triterpenoids has been achieved. A putative biomimetic tricyclization cascade is employed to forge a fused decalin-/oxepane ring system. The synthetic route proceeds to (+)-cupacinoxepin in seven steps and to (+)-onoceranoxide in eight steps in the longest linear sequence, when starting from geranyl chloride and (+)-sclareolide. The bioinspired epoxypolyene cyclization is supported by computational and enzymatic studies.

Graphical abstract: Bioinspired synthesis of pentacyclic onocerane triterpenoids

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Article information


Submitted
06 Sep 2017
Accepted
14 Oct 2017
First published
16 Oct 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 8285-8290
Article type
Edge Article

Bioinspired synthesis of pentacyclic onocerane triterpenoids

F. Bartels, Y. J. Hong, D. Ueda, M. Weber, T. Sato, D. J. Tantillo and M. Christmann, Chem. Sci., 2017, 8, 8285
DOI: 10.1039/C7SC03903D

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