Details
| Original language | English |
|---|---|
| Pages (from-to) | 4475-4477 |
| Number of pages | 3 |
| Journal | Organic Letters |
| Volume | 20 |
| Issue number | 15 |
| Early online date | 13 Jul 2018 |
| Publication status | Published - 3 Aug 2018 |
Abstract
The first total synthesis of pericoannosin A (1) containing 15 steps in the longest linear sequence with an overall yield of 5.5% is reported. The hybrid peptide-polyketide was isolated from the endophytic fungus Periconia sp. F-31 and bears a unique tricyclic core structure. The key steps are a glycolate aldol reaction and a Diels-Alder reaction utilizing an Evans auxiliary for controlling the stereochemistry. Furthermore, a late-stage equilibration was employed.
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. 20, No. 15, 03.08.2018, p. 4475-4477.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Total Synthesis of Pericoannosin A
AU - Lücke, Daniel
AU - Linne, Yannick
AU - Hempel, Katharina
AU - Kalesse, Markus
N1 - Publisher Copyright: © 2018 American Chemical Society. Copyright: Copyright 2018 Elsevier B.V., All rights reserved.
PY - 2018/8/3
Y1 - 2018/8/3
N2 - The first total synthesis of pericoannosin A (1) containing 15 steps in the longest linear sequence with an overall yield of 5.5% is reported. The hybrid peptide-polyketide was isolated from the endophytic fungus Periconia sp. F-31 and bears a unique tricyclic core structure. The key steps are a glycolate aldol reaction and a Diels-Alder reaction utilizing an Evans auxiliary for controlling the stereochemistry. Furthermore, a late-stage equilibration was employed.
AB - The first total synthesis of pericoannosin A (1) containing 15 steps in the longest linear sequence with an overall yield of 5.5% is reported. The hybrid peptide-polyketide was isolated from the endophytic fungus Periconia sp. F-31 and bears a unique tricyclic core structure. The key steps are a glycolate aldol reaction and a Diels-Alder reaction utilizing an Evans auxiliary for controlling the stereochemistry. Furthermore, a late-stage equilibration was employed.
UR - http://www.scopus.com/inward/record.url?scp=85050966281&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.8b01768
DO - 10.1021/acs.orglett.8b01768
M3 - Article
C2 - 30003789
AN - SCOPUS:85050966281
VL - 20
SP - 4475
EP - 4477
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 15
ER -