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RESEARCH ARTICLE
Contents Vol 69(12)

A Biomimetic Synthetic Approach to the Frondosins*

Kevin K. W. Kuan A , Aylin M. C. Hirschvogel A and Jonathan H. George A B
+ Author Affiliations
- Author Affiliations

A Department of Chemistry, University of Adelaide, Adelaide, SA 5005, Australia.

B Corresponding author. Email: jonathan.george@adelaide.edu.au

Australian Journal of Chemistry 69(12) 1420-1423 https://doi.org/10.1071/CH16218
Submitted: 4 April 2016  Accepted: 2 June 2016   Published: 20 July 2016

Abstract

The frondosins are a family of five marine sponge-derived meroterpenoids. We propose that the 6–7 ring system common to each of the frondosins is biosynthesized via ring expansion of a 6–6 ring system. Compelling evidence in favour of this proposal was obtained in the form of a biomimetic synthesis of the frondosin 6–7 ring system, which features a highly stereo- and regio-selective ring expansion cascade reaction as the key step.


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