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

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

doi:10.3987/com-06-s(k)32

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 journal › Article › peer-review

29 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 language	English
Pages (from-to)	421-438
Number of pages	18
Journal	Heterocycles
Volume	72
DOIs	https://doi.org/10.3987/com-06-s(k)32
Publication status	Published - Apr 13 2007
Externally published	Yes

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Pharmacology
Organic Chemistry

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10.3987/com-06-s(k)32

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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.",

author = "Hisashi Mihara and Tomoyuki Shibuguchi and Akiyoshi Kuramochi and Takashi Ohshima and Masakatsu Shibasaki",

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AU - Mihara, Hisashi

AU - Shibuguchi, Tomoyuki

AU - Kuramochi, Akiyoshi

AU - Ohshima, Takashi

AU - Shibasaki, Masakatsu

PY - 2007/4/13

Y1 - 2007/4/13

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AB - 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.

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JO - Heterocycles

JF - Heterocycles

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

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