Journal
ORGANIC LETTERS
Volume 19, Issue 17, Pages 4536-4539Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02112
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- spectroscopy department of the Institute of Organic Chemistry
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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.
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