Total synthesis of 10-deoxymethynolide the aglycon of the macrolide antibiotic 10-deoxymethymycin

被引：47
作者：
Pilli, RA
de Andrade, CKZ
Souto, CRO
de Meijere, A
机构：
[1] UNICAMP, Inst Quim, BR-13083970 Campinas, SP, Brazil
[2] Univ Gottingen, Inst Organ Chem, D-3400 Gottingen, Germany
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 22期
关键词：
D O I：
10.1021/jo9809433
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A short and efficient total synthesis of 10-deoxymethynolide (2c), the aglycon of 10-deoxymethymycin (1c), has been accomplished in 16 steps and 12% overall yield from (S)-3-O-p-toluenesulfonyl-3-hydroxy-2-methylpropanal (15c). The synthesis features an expeditious preparation of (+)-5a, a synthetic equivalent of the Prelog-Djerassi lactonic acid, and the construction of a 12-membered lactone through an intramolecular Nozaki-Hiyama-Kishi coupling reaction.
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页码：7811 / 7819
页数：9
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