Convergent Synthesis of Taxol Skeleton via Decarbonylative Radical Coupling Reaction

Hiroaki Matoba, Takahiro Watanabe, Masanori Nagatomo, Masayuki Inoue

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

The highly oxygenated 6/8/6-membered ABC-ring 2 of taxol was assembled in a convergent fashion. A decarbonylative radical reaction between α-alkoxyacyl telluride 4 and cyanocyclohexenone 5 linked the A- and C-rings and stereoselectively installed the C2- and C3-tertiary carbon centers of 3. After the C8-quaternary stereocenter was constructed, the C9-methyl ketone and the C11-vinyl triflate of 30 participated in Pd(0)-promoted cyclization of the eight-membered B-ring, giving rise to the taxol skeleton 2.

Original languageEnglish
Pages (from-to)7554-7557
Number of pages4
JournalOrganic letters
Volume20
Issue number23
DOIs
Publication statusPublished - 2018 Dec 7
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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