A biosynthetically-inspired synthesis of the tetrahydrofuran core of obtusallenes II and IV

被引:31
作者
Braddock, D. Christopher [1 ]
Bhuva, Roshni
Millan, David S.
Perez-Fuertes, Yolanda
Roberts, Craig A.
Sheppard, Richard N.
Solanki, Savade
Stokes, Elaine S. E.
White, Andrew J. P.
机构
[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
[2] AstraZeneca, Macclesfield SK10 4TG, Cheshire, England
[3] Pfizer Ltd, Global Res & Dev, Sandwich Labs, Sandwich CT13 9NJ, Kent, England
关键词
D O I
10.1021/ol062818g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Sharpless asymmetric dihydroxylation was regioselective for the trans olefin in an E vs Z vs terminal triene substrate. To test a biosynthetic hypothesis, the resulting diol underwent diastereoselective bromoetherification to provide the des-chloro core of marine natural products obtusallenes II and IV. Alternatively, anionic chloride ring-opening of a Z-beta,gamma-unsaturated epoxide gave separable regioisomeric halohydrins. Bromoetherification gave the fully elaborated core of obtusallenes II and IV with all of the relative stereochemistry correctly set.
引用
收藏
页码:445 / 448
页数:4
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