Concise enantioselective synthesis of (+)-aspicilin based on a ruthenium catalyzed olefin metathesis reaction

Toshiko Nishioka; Yoshiharu Iwabuchi; Hiroshi Irie; Susumi Hatakeyama

doi:10.1016/S0040-4039(98)01130-7

Concise enantioselective synthesis of (+)-aspicilin based on a ruthenium catalyzed olefin metathesis reaction

Toshiko Nishioka, Yoshiharu Iwabuchi, Hiroshi Irie, Susumi Hatakeyama

Research output: Contribution to journal › Article › peer-review

36 Citations (Scopus)

Abstract

An efficient enantioselective synthesis of (+)-aspicilin has been achieved in 12 steps from (2E,5E)-1,7-dibenzyloxy-2,5-heptadiene-4-ol employing Red-Al®-promoted reductive cleavage of the benzyl 4-hydroxy-2- butenyl ether structure and ruthenium catalyzed olefin metathesis as key steps.

Original language	English
Pages (from-to)	5597-5600
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	31
DOIs	https://doi.org/10.1016/S0040-4039(98)01130-7
Publication status	Published - 1998 Jul 30
Externally published	Yes

Keywords

Aspicilin
Asymmetric synthesis
Olefin metathesis
Polyol chiral building block

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(98)01130-7

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title = "Concise enantioselective synthesis of (+)-aspicilin based on a ruthenium catalyzed olefin metathesis reaction",

abstract = "An efficient enantioselective synthesis of (+)-aspicilin has been achieved in 12 steps from (2E,5E)-1,7-dibenzyloxy-2,5-heptadiene-4-ol employing Red-Al{\textregistered}-promoted reductive cleavage of the benzyl 4-hydroxy-2- butenyl ether structure and ruthenium catalyzed olefin metathesis as key steps.",

keywords = "Aspicilin, Asymmetric synthesis, Olefin metathesis, Polyol chiral building block",

author = "Toshiko Nishioka and Yoshiharu Iwabuchi and Hiroshi Irie and Susumi Hatakeyama",

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language = "English",

volume = "39",

pages = "5597--5600",

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T1 - Concise enantioselective synthesis of (+)-aspicilin based on a ruthenium catalyzed olefin metathesis reaction

AU - Nishioka, Toshiko

AU - Iwabuchi, Yoshiharu

AU - Irie, Hiroshi

AU - Hatakeyama, Susumi

PY - 1998/7/30

Y1 - 1998/7/30

N2 - An efficient enantioselective synthesis of (+)-aspicilin has been achieved in 12 steps from (2E,5E)-1,7-dibenzyloxy-2,5-heptadiene-4-ol employing Red-Al®-promoted reductive cleavage of the benzyl 4-hydroxy-2- butenyl ether structure and ruthenium catalyzed olefin metathesis as key steps.

AB - An efficient enantioselective synthesis of (+)-aspicilin has been achieved in 12 steps from (2E,5E)-1,7-dibenzyloxy-2,5-heptadiene-4-ol employing Red-Al®-promoted reductive cleavage of the benzyl 4-hydroxy-2- butenyl ether structure and ruthenium catalyzed olefin metathesis as key steps.

KW - Aspicilin

KW - Asymmetric synthesis

KW - Olefin metathesis

KW - Polyol chiral building block

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U2 - 10.1016/S0040-4039(98)01130-7

DO - 10.1016/S0040-4039(98)01130-7

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SN - 0040-4039

VL - 39

SP - 5597

EP - 5600

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 31

ER -

Concise enantioselective synthesis of (+)-aspicilin based on a ruthenium catalyzed olefin metathesis reaction

Abstract

Keywords

ASJC Scopus subject areas

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