Stereocontrolled synthesis of substituted bicyclic ethers through oxy-Favorskii rearrangement: Total synthesis of (±)-communiol e

Shoji Kobayashi*, Tatsuhiro Kinoshita, Takuji Kawamoto, Masato Wada, Hiroyuki Kuroda, Araki Masuyama, Ilhyong Ryu

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

The potential of the oxy-Favorskii rearrangement to form branched cis-fused bicyclic ethers was explored. Both tertiary and quaternary centers were constructed in highly stereospecific manners. Methanol and primary amines were effective nucleophiles for the rearrangement. The total synthesis of (±)-communiol E was achieved based on this method.

Original languageEnglish
Pages (from-to)7096-7103
Number of pages8
JournalJournal of Organic Chemistry
Volume76
Issue number17
DOIs
StatePublished - 2 Sep 2011

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