Abstract
We report a flexible stereocontrolled synthetic route to the southern fragment of lagunamides D and D’, two cytotoxic cyclodepsipeptides of the aurilides family. Key steps in the route include an anti-aldol Abiko-Masamune reaction and a Horner-Wadsworth-Emmonds (HWE) olefination. The key element of our synthetic strategy was the use of a pivotal intermediate, which owns the introduction a side-chain that differentiates the polyketide structure of the members of the family. Thus, to illustrate de synthetic potential of our strategy, we have also prepared four different advanced polyketide precursors.