Synthetic study of macquarimicins: Highly stereoselective construction of the AB-ring system

Ryosuke Munakata; Tatsuo Ueki; Hironori Katakai; Ken Ichi Takao; Kin Ichi Tadano

doi:10.1021/ol016449u

Synthetic study of macquarimicins: Highly stereoselective construction of the AB-ring system

Ryosuke Munakata, Tatsuo Ueki, Hironori Katakai, Ken Ichi Takao, Kin Ichi Tadano

Department of Applied Chemistry

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

34 Citations (Scopus)

Abstract

matrix presented The highly stereoselective synthesis of the AB-ring system of macquarimicins, a novel class of microbial metabolites with inhibitory activity for neutral sphingomyelinase, has been achieved. The present synthesis features the highly stereocontrolled construction of the cis-tetrahydroindan structure via the intramolecular Diels-Alder reaction of an (E,Z,E)-1,6,8-nonatriene derived from D-glyceraldehyde acetonide.

Original language	English
Pages (from-to)	3029-3032
Number of pages	4
Journal	Organic Letters
Volume	3
Issue number	19
DOIs	https://doi.org/10.1021/ol016449u
Publication status	Published - 2001 Sept 20

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol016449u

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abstract = "matrix presented The highly stereoselective synthesis of the AB-ring system of macquarimicins, a novel class of microbial metabolites with inhibitory activity for neutral sphingomyelinase, has been achieved. The present synthesis features the highly stereocontrolled construction of the cis-tetrahydroindan structure via the intramolecular Diels-Alder reaction of an (E,Z,E)-1,6,8-nonatriene derived from D-glyceraldehyde acetonide.",

author = "Ryosuke Munakata and Tatsuo Ueki and Hironori Katakai and Takao, {Ken Ichi} and Tadano, {Kin Ichi}",

year = "2001",

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T2 - Highly stereoselective construction of the AB-ring system

AU - Munakata, Ryosuke

AU - Ueki, Tatsuo

AU - Katakai, Hironori

AU - Takao, Ken Ichi

AU - Tadano, Kin Ichi

PY - 2001/9/20

Y1 - 2001/9/20

N2 - matrix presented The highly stereoselective synthesis of the AB-ring system of macquarimicins, a novel class of microbial metabolites with inhibitory activity for neutral sphingomyelinase, has been achieved. The present synthesis features the highly stereocontrolled construction of the cis-tetrahydroindan structure via the intramolecular Diels-Alder reaction of an (E,Z,E)-1,6,8-nonatriene derived from D-glyceraldehyde acetonide.

AB - matrix presented The highly stereoselective synthesis of the AB-ring system of macquarimicins, a novel class of microbial metabolites with inhibitory activity for neutral sphingomyelinase, has been achieved. The present synthesis features the highly stereocontrolled construction of the cis-tetrahydroindan structure via the intramolecular Diels-Alder reaction of an (E,Z,E)-1,6,8-nonatriene derived from D-glyceraldehyde acetonide.

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JO - Organic Letters

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Synthetic study of macquarimicins: Highly stereoselective construction of the AB-ring system

Abstract

ASJC Scopus subject areas

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