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Communication | Regular issue | Vol 48, No. 1, 1998, pp.5-10
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7991
Synthesis of Both Enantiomers of Four Different Macrocyclic Lactones

Yoshihiro Noda* and Hitoshi Kashin

*Department of Industrial Chemistry and Engineering, College of Engineering, Nihon University, Tamura-machi, Koriyama, Fukushima, 963-8642, Japan

Abstract

Both enantiomers of macrocyclic lactones, 12-tridecanolide (1), 13-tetradecanolide (2), 14-pentadecanolide (3) and 15-hexadecanolide (4), were synthesized utilizing (S)-(-)-β-hydroxythioacetal (5) as the chiral building block. Key steps are the C-alkylation of a dianion derived from 5 with alkyl dibromides followed by conversion of functional groups and the two macrolactonization. The both enantiomers of 1-4 have been obtained by reductive desulfurization of the dithiane moiety.