3 years ago

Total Synthesis of Nannocystin Ax

Total Synthesis of Nannocystin Ax
Markus Kalesse, Caroline Poock
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02112

DOI: 10.1021/acs.orglett.7b02112

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