Systematic synthesis of bis-THF ring cores in annonaceous acetogenins

被引:37
作者
Maezaki, N [1 ]
Kojima, N [1 ]
Tominaga, H [1 ]
Yanai, M [1 ]
Tanaka, T [1 ]
机构
[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan
关键词
D O I
10.1021/ol034131r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
graphic Systematic synthesis of bis-THF ring cores, synthetic intermediates of adjacent bis-THF annonaceous acetogenins, has been achieved by asymmetric alkynylation and subsequent stereodivergent THF ring formation. The asymmetric alkynylation of alpha-tetrahydrofuranic aldehyde with (S)-3-butyne-1,2-diol derivatives gave good yields of erythro- and threo-adducts with very high diastereoselectivity. These adducts were converted into four types of bis-THF cores via two kinds of one-pot THF ring formation.
引用
收藏
页码:1411 / 1414
页数:4
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