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Total Synthesis of Nannocystin Ax
Caroline Poock1, Markus Kalesse1,2
1Institute for Organic Chemistry and Centre of Biomolecular Drug Research (BMWZ) Leibniz Universität Hannover , Schneiderberg 1B, D-30167 Hannover, Germany.
Abstract:
The total synthesis of nannocystin Ax in an overall yield of 11% with 14 steps as the longest linear sequence is reported. Nannocystin Ax is a cytotoxic 21-membered depsipeptide and was isolated from the myxobacterial genus Nannocystis sp. The synthesis uses a vinylogous Horner-Wadsworth-Emmons reaction (HWE) and a vinylogous Mukaiyama aldol reaction (VMAR) as the key steps for the construction of the polyketide fragment. The macrocycle was closed via a macrolactamization reaction using COMU.
