Pseudopterosin synthesis from a chiral cross-conjugated hydrocarbon through a series of cycloadditions

Date

2015

Authors

Newton, Christopher
Drew, Samuel
Lawrence, Andrew
Willis, Anthony
Paddon-Row, Michael
Sherburn, Michael

Journal Title

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Volume Title

Publisher

Nature Publishing Group

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.

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Citation

Source

Nature Chemistry

Type

Journal article

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DOI

10.1038/nchem.2112

Restricted until

2037-12-31