A Facile and Efficient Synthesis of 4-Hydroxy-2,6-cis-tetrahydropyrans via Tandem Cross-Metathesis/Thermal SN2′ Reaction: Protecting-Group-Free Synthesis of (±)-Diospongin A

被引:48
作者
Lee, Kiyoun [1 ]
Kim, Hyoungsu [1 ]
Hong, Jiyong [1 ]
机构
[1] Duke Univ, Dept Chem, Durham, NC 27708 USA
关键词
STEREOSELECTIVE-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; 1,3-CHIRALITY TRANSFER; DIOSPONGIN-A; TETRAHYDROPYRAN; CYCLIZATION; OXYPALLADATION; TETRAHYDROFURANS; METHODOLOGY; SPIROKETAL;
D O I
10.1021/ol902125d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The tandem cross-metathesis/thermal S(N)2' reaction was explored for the facile and efficient synthesis of 4-hydroxy-2,6-cis-tetrahydropyrans. The mildness of the thermal conditions allowed for the synthesis of 4-hydroxy-2,6-cis-tetrahydropyrans from base-sensitive substrates without the use of protecting groups. The tandem reaction enabled a protecting-group-free synthesis of (+/-)-diospongin A.
引用
收藏
页码:5202 / 5205
页数:4
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