A practical synthesis of long-chain iso-fatty acids (iso-C12–C19) and related natural products

MB Richardson, SJ Williams

Index: Richardson, Mark B.; Williams, Spencer J. Beilstein Journal of Organic Chemistry, 2013 , vol. 9, p. 1807 - 1812

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Citation Number: 5

Abstract

Abstract A gram-scale synthesis of terminally-branched iso-fatty acids (iso-C 12–C 19) was developed commencing with methyl undec-10-enoate (methyl undecylenate)(for iso-C 12–C 14) or the C 15 and C 16 lactones pentadecanolide (for iso-C 15–C 17) and hexadecanolide (for iso-C 18–C 19). Central to the approaches outlined is the two-step construction of the terminal isopropyl group through addition of methylmagnesium bromide to the ester/ ...