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

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 03期

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

页码：445 / 448

页数：4

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