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Anionic heterogemini surfactants with –COOH, –SO 3 H and –PO(OH) 2  headgroups in combination were synthesized from Corynomicolic acid derivatives having R = C 11 H 23 . The –SO 3 H headgroup was obtained by the successive conversion of OH → OMs → SCN → SH → –SO 3 H. The PO(OH) 2  headgroup was introduced by the conjugate-addition to E-isomer of α,β-unsaturated ester derived from Corynomycolic acid ester. Heterogemini surfactant with –SO 3 H and –PO(OH) 2  headgroups was also synthesized from phosphonate analog of Corynomycolic acid. The stereoisomers (syn- and anti-isomers) of heterogemini surfactants were separately prepared except for heterogemini surfactants with –COOH and –PO(OH) 2  headgroups. Effects of variation and stereochemistry of two anionic headgroups on their surfactant properties were also studied on the basis of surface tension measurements.

A Novel Synthesis of Anionic Heterogemini Surfactants Containing COOH, SO 3 H and PO(OH) 2 Headgroups from Corynomicolic Acid and its Derivatives