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 -