Asymmetric synthesis of (+)- and (-)-streptenol A

Authors
Enders, D Hundertmark, T
Citation
D. Enders et T. Hundertmark, Asymmetric synthesis of (+)- and (-)-streptenol A, EUR J ORG C, (4), 1999, pp. 751-756
Citations number
27
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
4
Year of publication
1999
Pages
751 - 756
Database
ISI
SICI code
1434-193X(199904):4<751:ASO(A(>2.0.ZU;2-H
Abstract
The asymmetric synthesis of (+)-streptenol A was carried out in ten steps a nd with high enantioselectivity (ee greater than or equal to 96%). The key steps are the alpha-alkylation of 2,2-dimethyl-1,3-dioxan-5-one RAMP hydraz one A (1), subsequent deoxygenation and elaboration of the side chain via a ldehyde B to furnish (+)-streptenol A in 23% overall yield. In analogy, the enantiomer (-)-streptenol A was synthesized using the corresponding SAMP h ydrazone in 18% overall yield.