Tetrahedron p. 3335 - 3346 (1991)
Update date:2022-08-11
Topics:
Romeyke, Yvonne
Keller, Martin
Kluge, Heinz
Grabley, Susanne
Hammann, Peter
The enantioselective synthesis of all four stereoisomers of the secondary metabolite 3-hydroxy-5-decanolide (4a) from Cephalosporium recifei and both enatiomers of massoialactone (5a) by starting from one chiral building block, streptenol A (1a), a secondary metabolite from Streptomyces sp., is described.The key steps of the reaction sequence involve diastereoselective reduction of 1a to syn- or anti-triol 2a and 2b and the regioselective oxidation of the primary hydroxyl group.This reaction furnishes in one step the δ-lactones 3a and 3b and requires no protecting group.
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