Total Synthesis of Nannocystin Ax.

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Authors
Poock, Caroline
Kalesse, Markus
Issue Date
2017-09-01

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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.
Citation
Total Synthesis of Nannocystin Ax. 2017, 19 (17):4536-4539 Org. Lett.
Affiliation
Hemholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr. 7, 38124 Braunschweig, Germany.
Journal
Organic letters
URI
http://hdl.handle.net/10033/621129
DOI
10.1021/acs.orglett.7b02112
PubMed ID
28809579
Type
Article
Language
en
ISSN
1523-7052
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http://creativecommons.org/licenses/by-nc-sa/4.0/
Except where otherwise noted, this item's license is described as http://creativecommons.org/licenses/by-nc-sa/4.0/