國家衛生研究院 NHRI:Item 3990099045/4338

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Title:	Alpha-activated cross conjugated cycloalkenone systems in organic synthesis
Authors:	Wu, YK;Ly, TW;Shia, KS
Contributors:	Division of Biotechnology and Pharmaceutical Research
Abstract:	Under catalysis with an appropriate Lewis acid, the intermolecular Diels-Alder cycloaddition and intramolecular polyene cyclization of the alpha-activated cross conjugated cycloalkenone systems, possessing particularly increased dienophilicity/electrophilicity in the cross conjugated double bond, proceeded constantly with a high degree of stereochemical control, leading to a variety of synthetically useful molecules, which may serve as advanced intermediates towards many structurally challenging natural products, especially cis-clerodane diterpenoids. Mechanistically, an additional conjugated double bond incorporated into the cycloalkenone core of the titled systems might contribute synergistically to the classical secondary orbital effects, thus significantly enhancing the endo-to-ketone addition. In addition, a tandem multiple sigma-bond migration process, an enzymatic pathway prevalent in nature, was proposed to rationalize the formation of structurally unusual polyene-cyclization products occurring under standard chemical conditions.
Date:	2010-02
Relation:	Current Organic Synthesis. 2010 Feb;7(1):78-93.
Link to:	http://dx.doi.org/10.2174/157017910790820328
JIF/Ranking 2023:	http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=NHRI&SrcApp=NHRI_IR&KeyISSN=1570-1794&DestApp=IC2JCR
Cited Times(WOS):	https://www.webofscience.com/wos/woscc/full-record/WOS:000273774100005
Cited Times(Scopus):	http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=77953771762
Appears in Collections:	[Kak-Shan Shia] Periodical Articles

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