期刊
CHINESE JOURNAL OF ORGANIC CHEMISTRY
卷 35, 期 8, 页码 1615-1626出版社
SCIENCE PRESS
DOI: 10.6023/cjoc201504031
关键词
ortho-quinone methide; natural products; organic synthesis
资金
- National Natural Science Foundation of China [21472010, 91313303, 21222209]
ortho-Methylene cyclohexadienones, which are collectivelly referred to as ortho-quinone methides (o-QMs), were first suggested by Fries in 1907. o-QMs are a kind of short-lived and highly reactive versatile intermediates in organic synthesis. The unstability nature of o-QMs is due to their propensity to undergo rapid rearomatisation either by Michael addition of nucleophiles or, often more usefully, by cycloaddition with 2 pi partners or via oxa-6 pi-electrocyclisation to give benzopyrans. ortho-Quinone methides were always used in the synthesis of natural products through Michael addition and cycloaddition. As a new member of the family of inherently reactive species, ortho-quinone methides are similar with radicals, carbocations, carbenes, etc. And now using o-QMs to form skeletons of natural products has become a very useful stratergy. This review contains the major application in the synthesis of natural products during 2009 to 2014.
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