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

Authors
Munakata, R Ueki, T Katakai, H Takao, K Tadano, K
Citation
R. Munakata et al., Synthetic study of macquarimicins: Highly stereoselective construction of the AB-ring system, ORG LETT, 3(19), 2001, pp. 3029-3032
Citations number
41
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
19
Year of publication
2001
Pages
3029 - 3032
Database
ISI
SICI code
1523-7060(20010920)3:19<3029:SSOMHS>2.0.ZU;2-P
Abstract
[GRAPHICS] The highly stereoselective synthesis of the AB-ring system of macquarimicin s, a novel class of microbial metabolites with inhibitory activity for neut ral 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-nonatrlene derived from D-glyceraldehyde acetonide.