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Type: Journal article
Title: Pseudopterosin synthesis from a chiral cross-conjugated hydrocarbon through a series of cycloadditions
Author: Newton, C.
Drew, S.
Lawrence, A.
Willis, A.
Paddon-Row, M.
Sherburn, M.
Citation: Nature Chemistry, 2015; 7(1):82-86
Publisher: Nature Publishing Group
Issue Date: 2015
ISSN: 1755-4330
Statement of
Christopher G. Newton, Samuel L. Drew, Andrew L. Lawrence, Anthony C. Willis, Michael N. Paddon-Row and Michael S. Sherburn
Abstract: The pseudopterosins are a family of diterpene marine natural products, which, by virtue of their interesting anti-inflammatory and analgesic properties, have attracted the attentions of many synthetic chemists. The most efficient syntheses reported to date are 14 and 20 steps in the longest linear sequence for chiral pool and enantioselective approaches, respectively, and all start with precursors that are easily mapped onto the natural product structure. Here, we describe an unconventional approach in which a chiral cross-conjugated hydrocarbon is used as the starting material for a series of three cycloadditions. Our approach has led to a significant reduction in the step count required to access these interesting natural products (10 steps chiral pool and 11 steps enantioselective). Furthermore it demonstrates that cross-conjugated hydrocarbons, erroneously considered by many to be too unstable and difficult to handle, are viable precursors for natural product synthesis.
Keywords: Hydrocarbons
Description: Published Online: 17 November 2014
Rights: © 2014 Macmillan Publishers Limited. All rights reserved.
RMID: 0030084437
DOI: 10.1038/nchem.2112
Appears in Collections:Chemistry publications

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