Details
| Original language | English |
|---|---|
| Pages (from-to) | 6938-6942 |
| Number of pages | 5 |
| Journal | Angewandte Chemie |
| Volume | 60 |
| Issue number | 13 |
| Early online date | 15 Jan 2021 |
| Publication status | Published - 22 Mar 2021 |
Abstract
The first total synthesis of chondrochloren A is accomplished using a 1,2-metallate rearrangement addition as an alternative for the Nozaki-Hiyama-Kishi reaction. This transformation also avoids the inherent challenges of this polyketide segment and provides a new, unprecedented strategy to assemble polyketidal frameworks. The formation of the Z-enamide is accomplished using a Z-selective cross coupling of the corresponding amide to a Z-vinyl bromide.
Keywords
- 1,2-metallate rearrangement, chondrochloren, Hoppe anion, natural product synthesis, polyketides
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
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In: Angewandte Chemie , Vol. 60, No. 13, 22.03.2021, p. 6938-6942.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - The Total Synthesis of Chondrochloren A
AU - Linne, Yannick
AU - Bonandi, Elisa
AU - Tabet, Christopher
AU - Geldsetzer, Jan
AU - Kalesse, Markus
PY - 2021/3/22
Y1 - 2021/3/22
N2 - The first total synthesis of chondrochloren A is accomplished using a 1,2-metallate rearrangement addition as an alternative for the Nozaki-Hiyama-Kishi reaction. This transformation also avoids the inherent challenges of this polyketide segment and provides a new, unprecedented strategy to assemble polyketidal frameworks. The formation of the Z-enamide is accomplished using a Z-selective cross coupling of the corresponding amide to a Z-vinyl bromide.
AB - The first total synthesis of chondrochloren A is accomplished using a 1,2-metallate rearrangement addition as an alternative for the Nozaki-Hiyama-Kishi reaction. This transformation also avoids the inherent challenges of this polyketide segment and provides a new, unprecedented strategy to assemble polyketidal frameworks. The formation of the Z-enamide is accomplished using a Z-selective cross coupling of the corresponding amide to a Z-vinyl bromide.
KW - 1,2-metallate rearrangement
KW - chondrochloren
KW - Hoppe anion
KW - natural product synthesis
KW - polyketides
UR - http://www.scopus.com/inward/record.url?scp=85101587803&partnerID=8YFLogxK
U2 - 10.1002/anie.202016072
DO - 10.1002/anie.202016072
M3 - Article
C2 - 33450788
AN - SCOPUS:85101587803
VL - 60
SP - 6938
EP - 6942
JO - Angewandte Chemie
JF - Angewandte Chemie
SN - 1433-7851
IS - 13
ER -