Details
| Original language | English |
|---|---|
| Pages (from-to) | 670-673 |
| Number of pages | 4 |
| Journal | Beilstein Journal of Organic Chemistry |
| Volume | 16 |
| Publication status | Published - 14 Apr 2020 |
Abstract
The stereoselective synthesis of the (Z)-enamide fragment of chondrochloren (1) is described. A Buchwald-type coupling between amide 3 and (Z)-bromide 4 was used to generate the required fragment. The employed amide 3 comprising three chiral centers was obtained through a seven-step sequence starting from D-ribonic acid-1,4-lactone. The (Z)-vinyl bromide 4 is accessible in four steps from 4-hydroxybenzaldehyde. The pivotal cross coupling between both fragments was achieved after extensive experimentation with copper(I) iodide, K2CO3 and N,N′-dimethylethane-1,2-diamine.
Keywords
- Cross coupling, Myxobacteria, Natural product, Ribolactone, Z-enamide
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
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In: Beilstein Journal of Organic Chemistry, Vol. 16, 14.04.2020, p. 670-673.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Towards the total synthesis of chondrochloren A
T2 - Synthesis of the (Z)-enamide fragment
AU - Geldsetzer, Jan
AU - Kalesse, Markus
N1 - Funding Information: We are grateful to the DFG (Ka913/24-1) and the graduate school MINAS for funding this research.
PY - 2020/4/14
Y1 - 2020/4/14
N2 - The stereoselective synthesis of the (Z)-enamide fragment of chondrochloren (1) is described. A Buchwald-type coupling between amide 3 and (Z)-bromide 4 was used to generate the required fragment. The employed amide 3 comprising three chiral centers was obtained through a seven-step sequence starting from D-ribonic acid-1,4-lactone. The (Z)-vinyl bromide 4 is accessible in four steps from 4-hydroxybenzaldehyde. The pivotal cross coupling between both fragments was achieved after extensive experimentation with copper(I) iodide, K2CO3 and N,N′-dimethylethane-1,2-diamine.
AB - The stereoselective synthesis of the (Z)-enamide fragment of chondrochloren (1) is described. A Buchwald-type coupling between amide 3 and (Z)-bromide 4 was used to generate the required fragment. The employed amide 3 comprising three chiral centers was obtained through a seven-step sequence starting from D-ribonic acid-1,4-lactone. The (Z)-vinyl bromide 4 is accessible in four steps from 4-hydroxybenzaldehyde. The pivotal cross coupling between both fragments was achieved after extensive experimentation with copper(I) iodide, K2CO3 and N,N′-dimethylethane-1,2-diamine.
KW - Cross coupling
KW - Myxobacteria
KW - Natural product
KW - Ribolactone
KW - Z-enamide
UR - http://www.scopus.com/inward/record.url?scp=85084386392&partnerID=8YFLogxK
U2 - 10.3762/bjoc.16.64
DO - 10.3762/bjoc.16.64
M3 - Article
AN - SCOPUS:85084386392
VL - 16
SP - 670
EP - 673
JO - Beilstein Journal of Organic Chemistry
JF - Beilstein Journal of Organic Chemistry
SN - 1860-5397
ER -