Synthesis of macrotetrolide alpha, a designed polynactin analog composed of (+)- and (-)-bishomononactic acids.

Macrotetrolide alpha, a designed analog of polynactin composed of (+)- and (-)-bishomononactic acids, was synthesized. These monomers were prepared via optical resolution of the corresponding (S)-O-acetylmandelates. Assembly of the monomers to macrotetrolide alpha took seven steps without any loss of the intermediates.

Synthesis of (+/-)-methyl bishomononactate, a monomeric component of polynactin antibiotics.

The synthesis of (+/-)-methyl bishomononactate, one of the monomeric components of polynactin antibiotics (macrotetrolides), was achieved via cis-selective iodoetherification as the key step.