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由二甲氧基酚製備雙環[3.2.1]辛酮之骨架
Thesis

由二甲氧基酚製備雙環[3.2.1]辛酮之骨架

陳靜嫻
Masters, National Tsing Hua University
2003

Abstract

雙環[3.2.1]雙環[2.2.2]辛烯酮掩飾鄰苯?Diels-Alder反應三環[3.3.0.02,8]辛-3-酮氧-雙烯-甲烷重排反應氫化三正丁基錫二乙醯氧基碘(III)苯還原開環法環丙烷開環法 Diels-Alder reactionoxa-di-π-methane rearrangementODPMmasked-o-benzoquinonebicycle[3.2.1]tricyclo[3.3.0.02,8]octan-3-onebicycle[2.2.2]octenoneDAIBn-Bu3SnHring-opening
Because of their widespread occurrence in a large variety of natural products, for example, drechslerines A and B bicycle[3.2.1]octanones remain a focus of attention for synthetic organic chemists. Recently, we have found that the bicyclo[2.2.2]octenone derivatives, which can be obtained from the Diels-Alder reaction of masked-o-benzoquinone with various dienophiles, upon direct irradiation in acetone furnished the ODPM (oxa-di-π-methane) rearrangement product. Herein we propose a route to bicycle[3.2.1]octanone derivatives via opening the three-member ring of tricyclo[3.3.0.02,8]octan-3-one.

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