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

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

Research output: Contribution to journalArticle

23 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

Fingerprint

Cyclization
Ammonium Compounds
Salts
lepadiformine
tartaric acid
cylindricine C

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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.

Short synthesis of (+)-cylindricine C and formal total synthesis of (-)-lepadiformine. / Mihara, Hisashi; Shibuguchi, Tomoyuki; Kuramochi, Akiyoshi; Ohshima, Takashi; Shibasaki, Masakatsu.

In: Heterocycles, Vol. 72, 13.04.2007, p. 421-438.

Research output: Contribution to journalArticle

Mihara, H, Shibuguchi, T, Kuramochi, A, Ohshima, T & Shibasaki, M 2007, 'Short synthesis of (+)-cylindricine C and formal total synthesis of (-)-lepadiformine', Heterocycles, vol. 72, pp. 421-438.
Mihara H, Shibuguchi T, Kuramochi A, Ohshima T, Shibasaki M. Short synthesis of (+)-cylindricine C and formal total synthesis of (-)-lepadiformine. Heterocycles. 2007 Apr 13;72:421-438.
Mihara, Hisashi ; Shibuguchi, Tomoyuki ; Kuramochi, Akiyoshi ; Ohshima, Takashi ; Shibasaki, Masakatsu. / Short synthesis of (+)-cylindricine C and formal total synthesis of (-)-lepadiformine. In: Heterocycles. 2007 ; Vol. 72. pp. 421-438.
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