Aldol condensation reactions of chiral (dienone) tricarbonyliron complexes. 21. Enantioselective synthesis of the dienic polyols streptenols C and D (metabolites from Streptomyces Fimbriatus)

✍ Scribed by Michel Franck-Neumann; Paul Bissinger; Philippe Geoffroy

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 250 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)00904-0

✦ Synopsis

The trimethylsilyl enol ether of (3,5-heptadien-2-one) tricarbonyliron 1 undergoes a highly stereoselective cross aldol reaction with TiCl4-coordinated I]-o.methoxybenzyloxypropanal yielding after deprotection the ketodiol complex 9. Direct decomplexation or decomplexation after totally metal induced stereoselecfive reduction to the triol 10, led to Streptenols C and D. The natural dextrorotatory enantiomers were obtained from the readily available pure (+)-1.