ALDOL CONDENSATION-REACTIONS OF CHIRAL (DIENONE) TRICARBONYLIRON COMPLEXES .2. ENANTIOSELECTIVE SYNTHESIS OF THE DIENIC POLYOLS STREPTENOL-C AND STREPTENOL-D (METABOLITES FROM STREPTOMYCES FIMBRIATUS)

Authors
FRANCKNEUMANN M BISSINGER P GEOFFROY P
Citation
M. Franckneumann et al., ALDOL CONDENSATION-REACTIONS OF CHIRAL (DIENONE) TRICARBONYLIRON COMPLEXES .2. ENANTIOSELECTIVE SYNTHESIS OF THE DIENIC POLYOLS STREPTENOL-C AND STREPTENOL-D (METABOLITES FROM STREPTOMYCES FIMBRIATUS), Tetrahedron letters, 38(25), 1997, pp. 4469-4472
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
25
Year of publication
1997
Pages
4469 - 4472
Database
ISI
SICI code
0040-4039(1997)38:25<4469:ACOC(T>2.0.ZU;2-Z
Abstract
The trimethylsilyl enol ether of (3,5-heptadien-2-one) tricarbonyliron 1 undergoes a highly stereoselective cross aldol reaction with TiCl4- coordinated beta-o.methoxybenzyloxypropanal yielding after deprotectio n the ketodiol complex 9. Direct decomplexation or decomplexation afte r totally metal induced stereoselective reduction to the triol 10, led to Streptenols C and D. The natural dextrorotatory enantiomers were o btained from the readily available pure (+)-1. (C) 1997 Elsevier Scien ce Ltd.