Synthesis of the ABC ring system of paclitaxel: Formation of the 8-membered B ring by intramolecular alkylation

S. Miyamoto, T. Doi, T. Takahashi

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

The formation of the B ring of the ABC ring system of paclitaxel was accomplished by intramolecular alkylation of the protected cyanohydrin ether in the presence of the 7-alkoxy group on the C ring. A significant effect of the protective groups at the 1,2-positions was observed in this alkylation. Acyclic protection provided the desired compound 3c and 3d in moderate yields, whereas cyclic protection led to 3a in low yield.

Original languageEnglish
Pages (from-to)97-99
Number of pages3
JournalSynlett
Issue number1
DOIs
Publication statusPublished - 2002 Jan 1
Externally publishedYes

Keywords

  • Cyanohydrins
  • Intramolecular alkylations
  • Paclitaxel
  • Terpenoids

ASJC Scopus subject areas

  • Organic Chemistry

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