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Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment.

Geldsetzer, Jan
; 
Kalesse, Markus
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Issue Date
2020-04-14
Submitted date
2022-05-06
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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 ᴅ-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.
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Journal
Beilstein journal of organic chemistry
URI
http://hdl.handle.net/10033/623186
DOI
10.3762/bjoc.16.64
PubMed ID
32362944
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Article
Language
en
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ISSN
1860-5397
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Attribution 4.0 International
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publications of the department medicinal chemistry (MCH)