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

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 22期

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

页码：5202 / 5205

页数：4