Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment.
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Issue Date
2020-04-14Submitted date
2022-05-06
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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.PubMed ID
32362944Type
ArticleLanguage
enISSN
1860-5397ae974a485f413a2113503eed53cd6c53
10.3762/bjoc.16.64
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- Creative Commons
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