The dihydrofuran template approach to furofuran synthesis

被引：27
作者：
Aldous, David J.
Batsanov, Andrei S.
Yufit, Dmitrii S.
Dalencon, Anne J.
Dutton, William M.
Steel, Patrick G.
机构：
[1] Univ Durham, Dept Chem, Durham DH1 3LE, England
[2] Sanofi Aventis Pharma Inc, Bridgewater, NJ 08807 USA
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2006年 / 4卷 / 15期
关键词：
D O I：
10.1039/b604952d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Flash vacuum pyrrolysis of vinyl epoxides provides cis-dihydrofuran carboxylic esters in good yields and diastereoselectivities, which, on base-promoted epimerisation afford the complementary trans series. The compounds provide a viable template for a Lewis acid promoted cyclisation to provide the 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane core found in the furofuran series of natural lignans. This strategy is stereodivergent and can be controlled to provide the exo-exo, exo-endo or endo-endo stereochemistries. The approach has been exemplified in syntheses of the sesamyl furofurans (+/-)-epiasarinin and (+/-)-asarinin.
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收藏
页码：2912 / 2927
页数：16
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