Stereocontrolled Synthesis of Multisubstituted 1,3-Dienes via an Allene-Claisen Rearrangement

Kenji Matsumoto, Naoyuki Mizushina, Masahiro Yoshida, Mitsuru Shindo

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Abstract

We herein developed a stereoselective synthetic method for the preparation of multisubstituted 1,3-dienes via an allene-Claisen rearrangement. The Claisen rearrangement of anti -allenyl alcohols provided (1 E,3 Z)-1,3-dienes, which are essential components of bongkrekic acid, in high stereoselectivities. To demonstrate the synthetic utility of the resulting 1,3-dienes, further functional transformations and Diels-Alder reactions are described.

Original languageEnglish
Article numberst-2017-u0300-l
Pages (from-to)2340-2344
Number of pages5
JournalSynlett
Volume28
Issue number17
DOIs
Publication statusPublished - Oct 23 2017

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All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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