Synthesis of Malyngolide, an Antibiotic from the Marine Blue-Green Alga Lyngbya majuscula Gomont

Article abstract of DOI:10.1021/jo00325a002

Malyngolide (1) was synthetized, starting from the condensation of dianion 2, obtained by metalation with lithium diisopropylamide of the sodium salt of tiglic acid, and decanal.Successive esterification of 3a and oxidation with Jones reagent of 4a afforded 5 in very good yield.Olefination of 5 with methylenemagnesium iodide gave 6, which was converted to the corresponding iodolactone 7.Hydrolysis of 7 to 1 was accomplished by Hg(ClO4)2 in dimethoxyethane/water (path A).Malyngolide (1) was also obtained by condensation of 2 with2-<(2-oxoundec-1-yl)oxy>tetrahydropyran (9b).Removal of the THP protecting group in 10 by 6 N HCl affords 1 (path B).