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. 2018 Jul 6;20(13):3883-3887.
doi: 10.1021/acs.orglett.8b01464. Epub 2018 Jun 13.

A Nitrone Dipolar Cycloaddition Strategy toward an Enantioselective Synthesis of Massadine

Jeffrey S Cannon  1
Affiliations

A Nitrone Dipolar Cycloaddition Strategy toward an Enantioselective Synthesis of Massadine

Jeffrey S Cannon. Org Lett. .

Abstract

An enantioselective route to the C,D-bicycle of massadine is reported. Enantiopure intermediates were generated by a single stereoselective reduction using the Corey-Bakshi-Shibata reagent. This initial stereoinduction was translated into the five contiguous stereocenters of the massadine D-ring by a synthetic route that features a diastereoselective and stereospecific Ireland-Claisen rearrangement of a trianionic enolate followed by a diastereoselective nitrone dipolar cycloaddition of a highly electron-poor oxime.

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Conflict of interest statement

The author declares no competing financial interest.

Figures

Scheme 1.
Scheme 1.
Retrosynthetic Analysis
Scheme 2.
Scheme 2.
Allylic Ester Synthesis
Scheme 3.
Scheme 3.
Synthesis of Oxime Substrates
Scheme 4.
Scheme 4.
Conversion to Functionalized Cyclopentane
Scheme 5.
Scheme 5.
Synthesis of C-Ring
See this image and copyright information in PMC

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