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The formal asymmetric synthesis of (...

Lee, Che-Wah.

The formal asymmetric synthesis of (plus)-epoxysorbicillinol.

紀錄類型:	書目-電子資源 : Monograph/item
正題名/作者:	The formal asymmetric synthesis of (plus)-epoxysorbicillinol.
作者:	Lee, Che-Wah.
面頁冊數:	405 p.
附註:	Director: John Louis Wood.
附註:	Source: Dissertation Abstracts International, Volume: 66-11, Section: B, page: 5985.
Contained By:	Dissertation Abstracts International66-11B.
標題:	Chemistry, Organic.
電子資源:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3194676
ISBN:	9780542394416

The formal asymmetric synthesis of (plus)-epoxysorbicillinol.
Lee, Che-Wah.

The formal asymmetric synthesis of (plus)-epoxysorbicillinol. - 405 p.

Director: John Louis Wood.

Thesis (Ph.D.)--Yale University, 2005.

Enantiomerically pure acid 149 was elaborated in ten steps to the enantiopure alpha-diazoketone 158, which then underwent a highly chemoselective, rhodium catalyzed [3+2] cycloaddition reaction with allyl propiolate to give oxabicycle 203 as a single diastereomer in very good yield. This key step furnished the carbocyclic core of epoxysorbicillinol as a single enantiomer, and the oxabicycle obtained from this step is currently our most advanced enantiopure intermediate. A racemic version of oxabicycle 203 was then prepared and successfully advanced in six steps to dihydro-epoxysorbicillinol (95), which is a formal intermediate prepared in the prior racemic synthesis of epoxysorbicllinol.

ISBN: 9780542394416Subjects--Topical Terms:

193634
Chemistry, Organic.

The formal asymmetric synthesis of (plus)-epoxysorbicillinol.
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245 1 4 $a The formal asymmetric synthesis of (plus)-epoxysorbicillinol.
300 $a 405 p.
500 $a Director: John Louis Wood.
500 $a Source: Dissertation Abstracts International, Volume: 66-11, Section: B, page: 5985.
502 $a Thesis (Ph.D.)--Yale University, 2005.
520 # $a Enantiomerically pure acid 149 was elaborated in ten steps to the enantiopure alpha-diazoketone 158, which then underwent a highly chemoselective, rhodium catalyzed [3+2] cycloaddition reaction with allyl propiolate to give oxabicycle 203 as a single diastereomer in very good yield. This key step furnished the carbocyclic core of epoxysorbicillinol as a single enantiomer, and the oxabicycle obtained from this step is currently our most advanced enantiopure intermediate. A racemic version of oxabicycle 203 was then prepared and successfully advanced in six steps to dihydro-epoxysorbicillinol (95), which is a formal intermediate prepared in the prior racemic synthesis of epoxysorbicllinol.
520 # $a The vertinoid polyketides are a structurally diverse group of fungal metabolites which possess a wide range of interesting biological activity. Over the past several decades, 18 members of this class have been isolated and characterized, and several of them have exhibited significant activity as both free-radical scavengers and suppressors of TNF-alpha gene expression. Epoxysorbicillinol, the most recently discovered member of the vertinoid polyketide family, was isolated from a saltwater culture of Trichoderma longibrachiatum in 1998. Herein is described the first formal asymmetric synthesis of epoxysorbicillinol.
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