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

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

Research output: Contribution to journalArticle

32 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 languageEnglish
Pages (from-to)3029-3032
Number of pages4
JournalOrganic Letters
Volume3
Issue number19
DOIs
Publication statusPublished - 2001 Sep 20

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Sphingomyelin Phosphodiesterase
Cycloaddition Reaction
Diels-Alder reactions
metabolites
rings
synthesis
Metabolites
matrices
glyceraldehyde acetonide

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Synthetic study of macquarimicins : Highly stereoselective construction of the AB-ring system. / Munakata, Ryosuke; Ueki, Tatsuo; Katakai, Hironori; Takao, Kenichi; Tadano, Kin Ichi.

In: Organic Letters, Vol. 3, No. 19, 20.09.2001, p. 3029-3032.

Research output: Contribution to journalArticle

Munakata, Ryosuke ; Ueki, Tatsuo ; Katakai, Hironori ; Takao, Kenichi ; Tadano, Kin Ichi. / Synthetic study of macquarimicins : Highly stereoselective construction of the AB-ring system. In: Organic Letters. 2001 ; Vol. 3, No. 19. pp. 3029-3032.
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