Details
| Original language | English |
|---|---|
| Pages (from-to) | 4536-4539 |
| Number of pages | 4 |
| Journal | Organic letters |
| Volume | 19 |
| Issue number | 17 |
| Early online date | 15 Aug 2017 |
| Publication status | Published - 1 Sept 2017 |
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.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: Organic letters, Vol. 19, No. 17, 01.09.2017, p. 4536-4539.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Total Synthesis of Nannocystin Ax
AU - Poock, Caroline
AU - Kalesse, Markus
N1 - Publisher Copyright: © 2017 American Chemical Society. Copyright: Copyright 2017 Elsevier B.V., All rights reserved.
PY - 2017/9/1
Y1 - 2017/9/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85028769197&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.7b02112
DO - 10.1021/acs.orglett.7b02112
M3 - Article
C2 - 28809579
AN - SCOPUS:85028769197
VL - 19
SP - 4536
EP - 4539
JO - Organic letters
JF - Organic letters
SN - 1523-7060
IS - 17
ER -