Stereoselective one-pot three-component coupling approach towards the synthesis of the AC ring system of taxanes

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

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

The stereoselective one-pot three-component coupling reaction was accomplished by 1,4-addition of the protected cyanohydrin ether 9f to cyclohexenone 10g and subsequent addition of the resulting enolate to formaldehyde in high yield for the formation of the AC ring system of taxanes. We found that the bulky substituents at the 10-position in the A ring prevent the desired 1,4-addition. Similarly, the bulky trialkylsiloxy groups at the 4-position in the C ring prevent the 1,4-addition and electron-donating alkoxy groups at the same position induce the undesired retro-Michael reaction.

Original languageEnglish
Pages (from-to)3408-3410
Number of pages3
JournalTetrahedron Letters
Volume50
Issue number26
DOIs
Publication statusPublished - 2009 Jul 1

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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