Formal total synthesis of (+)-wortmannin using catalytic asymmetric intramolecular aldol condensation reaction

Hiroki Shigehisa, Takashi Mizutani, Shin Ya Tosaki, Takashi Ohshima, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

64 Citations (Scopus)

Abstract

A catalytic process for the synthesis of optically active C4-substituted tetrahydroindandiones using an asymmetric intramolecular aldol condensation reaction was developed. When 30 mol% of phenylalanine and 50 mol% of pyridinium p-toluenesulfonate were used under highly concentrated conditions, a variety of C4-substituted tetrahydroindandiones and octahydronaphthalenediones were obtained in high yield (up to 89% yield) and high enantiomeric excess (up to 94% ee). One of the products was successfully transformed into the key intermediate for the synthesis of the phosphatidylinositol 3-kinase inhibitor wortmannin, achieving formal total synthesis of (+)-wortmannin.

Original languageEnglish
Pages (from-to)5057-5065
Number of pages9
JournalTetrahedron
Volume61
Issue number21
DOIs
Publication statusPublished - May 23 2005
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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