Synthetic approaches to the manumycin A, B and C antibiotics: The first total synthesis of (+)-manumycin A

被引:43
作者
Alcaraz, L
Macdonald, G
Ragot, J
Lewis, NJ
Taylor, RJK [1 ]
机构
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
[2] SmithKline Beecham Pharmaceut, Tonbridge TN11 9AN, Kent, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/S0040-4020(98)00879-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of Manumycin A, as its (+)-enantiomer, is reported. The synthetic route features an asymmetric epoxidation (based on Wynberg's chiral phase transfer methodology) for the preparation of the key epoxyquinol nucleus, and a further demonstration of the utility of the Stille reaction for the construction of the Manumycin lower side chain. This synthesis of Manumycin A corrects the original stereochemical assignment and confirms the syn-hydroxy epoxide arrangement. The first syntheses of the quinones obtained by the oxidative degradation of Manumycins A-C are also described. (C) 1999 Elsevier Science Ltd. All rights reserved.
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页码:3707 / 3716
页数:10
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