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Total Synthesis of (-)-Nakadomarin A

J Stephen Clark¹, Chao Xu²

¹WestCHEM, School of Chemistry, Joseph Black Building, University of Glasgow, University Avenue, Glasgow, G12 8QQ, UK. stephen.clark@glasgow.ac.uk.

Angewandte Chemie (International Ed. in English)

|March 1, 2016

Abstract:

A highly efficient 12-step synthesis of the marine alkaloid (-)-nakadomarin A has been accomplished. The key advanced intermediate, a tetracyclic ketone derivative, was constructed in just seven steps using a sequence that includes an asymmetric Pauson-Khand reaction, an Overman rearrangement reaction, a ring-closing metathesis reaction, and an amination reaction. Late introduction of the furan ring during the synthesis of (-)-nakadomarin A means that the key tetracyclic ketone derivative has the potential to serve as an advanced intermediate for the synthesis of related marine alkaloids.

Keywords:

Overman rearrangement alkaloids natural products ring-closing metathesis total synthesis

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