Synthetic Studies on Leptolyngbyalides A–C: Stereoselective Synthesis of the C16–C27 Fragment

Abstract

Leptolyngbyalides A–C, isolated from the cyanobacterium Leptolyngbya sp. PCC 7375, are complex polyol macrolides, which are structurally relevant to oscillariolide and phormidolides A–C. We describe herein a stereoselective synthesis of the C16–C27 fragment of leptolyngbyalides, which involved an Evans syn-aldol reaction, a Kiyooka aldol reaction, and a Mukaiyama aldol reaction to construct the carbon chain with simultaneous generation of the stereogenic centers with full stereocontrol.