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Issue 41, 2016
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Preparation of oxocene terpenes. The first enantiospecific synthesis of cytotoxic arenaran A

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Abstract

The first syntheses of cytotoxic marine arenarans A and B starting from commercial (−)-sclareol are reported. The oxocene ring of the target compound is formed via ring-closing metathesis, a process that depends on certain structural requirements. The trans-fused structure of the natural product is confirmed by comparison with the cis-fused isomer, which was synthesized. This synthetic strategy is also applicable to the synthesis of other oxocene terpenes.

Graphical abstract: Preparation of oxocene terpenes. The first enantiospecific synthesis of cytotoxic arenaran A

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Supplementary files

Article information


Submitted
29 Jul 2016
Accepted
20 Sep 2016
First published
20 Sep 2016

This article is Open Access

Org. Biomol. Chem., 2016,14, 9836-9845
Article type
Paper

Preparation of oxocene terpenes. The first enantiospecific synthesis of cytotoxic arenaran A

A. Torres, P. Gutierrez, R. Alvarez-Manzaneda, R. Chahboun and E. Alvarez-Manzaneda, Org. Biomol. Chem., 2016, 14, 9836
DOI: 10.1039/C6OB01640E

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