Diastereoselective syntheses of chroman spiroketals via [4+2] cycloaddition of enol ethers and o-quinone methides

被引:91
作者
Marsini, Maurice A. [1 ]
Huang, Yaodong [1 ]
Lindsey, Christopher C. [1 ]
Wu, Kun-Liang [1 ]
Pettus, Thomas R. R. [1 ]
机构
[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
关键词
D O I
10.1021/ol8003244
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of chroman spiroketals are synthesized via inverse-demand [4 + 2] cycloaddition of enol ethers and ortho-quinone methides (o-QMs). Low temperature o-QM generation in situ allows for the kinetic, diastereoselective construction of these motifs, providing entry to a number of unusual chroman spiroketal natural products.
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页码:1477 / 1480
页数:4
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