期刊
ORGANIC LETTERS
卷 12, 期 20, 页码 4698-4701出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol102201z
关键词
-
资金
- National Science Foundation [NSF-CHE 0749918]
A blueprint for controlling the stereochemistry of oxygenated 5,5-spiroketals using chelation effects is provided. Chelation specifically of zinc salts (other protic and Lewis acids were less effective) between the spiroketal oxygen and an appropriately positioned alcohol group overrides normal biases in the preparation of 5,5-spiroketals, as illustrated by the stereocontrolled synthesis of epimeric cephalosporolide H isomers. This study provides new and valuable information for prescribing the chirality of the stereogenic core of 5,5-spiroketals.
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