Short synthesis of (+)-cylindricine C and formal total synthesis of (-)-lepadiformine

Hisashi Mihara, Tomoyuki Shibuguchi, Akiyoshi Kuramochi, Takashi Ohshima, Masakatsu Shibasaki

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24 Citations (Scopus)

Abstract

A short synthesis of (+)-cylindricine C (1c) and a formal total synthesis of (-)-lepadiformine (2) were achieved. The key strategy for the syntheses was a catalytic asymmetric Michael reaction using a two-center organocatalyst (11) (TaDiAS: Tartrate-derived Di-Ammonium Salt) and tandem cyclization to construct the tricyclic ring system.

Original languageEnglish
Pages (from-to)421-438
Number of pages18
JournalHeterocycles
Volume72
Publication statusPublished - Apr 13 2007
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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  • Cite this

    Mihara, H., Shibuguchi, T., Kuramochi, A., Ohshima, T., & Shibasaki, M. (2007). Short synthesis of (+)-cylindricine C and formal total synthesis of (-)-lepadiformine. Heterocycles, 72, 421-438.