Construction of the ABC ring system of taxanes via stereoselective one-pot three-component coupling and intramolecular alkylation of a protected cyanohydrin ether

Takayuki Serizawa, Shigeru Miyamoto, Shinichiro Fuse, Takayuki Doi, Takashi Takahashi

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Construction of the ABC ring system of taxanes via one-pot three-component coupling and intramolecular alkylation is accomplished. The 1,4-addition of a protected cyanohydrin ether to 2-methyl-2-cyclohexenone and subsequent addition of the resulting enolate to formaldehyde proceeded stereoselectively to provide the AC ring in 90% yield. The stereoselective reduction of the 2-keto group was achieved by using hydroxy-directed hydride reduction with LiAlH4. The intramolecular alkylation of the protected cyanohydrin ether furnished the ABC ring system of taxanes in 43% yield.

Original languageEnglish
Pages (from-to)942-949
Number of pages8
JournalBulletin of the Chemical Society of Japan
Volume83
Issue number8
DOIs
Publication statusPublished - 2010 Aug 26

ASJC Scopus subject areas

  • Chemistry(all)

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