Total synthesis of (–)-nakadomarin A

Clark, J. S. and Xu, C. (2016) Total synthesis of (–)-nakadomarin A. Angewandte Chemie (International Edition), 55(13), pp. 4332-4335. (doi:10.1002/anie.201600990)

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Abstract

A highly efficient 12-step synthesis of the marine alkaloid (−)-nakadomarin A has been accomplished. The key advanced intermediate, tetracyclic ketone 13, 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 C) during the synthesis of (−)-nakadomarin A means that the tetracyclic ketone 13 has the potential to serve as an advanced intermediate for the synthesis of related marine alkaloids.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Clark, Professor Stephen
Authors: Clark, J. S., and Xu, C.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Angewandte Chemie (International Edition)
Publisher:Wiley - V C H Verlag GmbH & Co. KGaA
ISSN:1433-7851
ISSN (Online):1521-3773
First Published:First published in Angewandte Chemie (International Edition) 128(13):4404-4407
Publisher Policy:Reproduced in accordance with the copyright policy of the publisher

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