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The diastereoselective Pauson-Khand ...

Miller, Stefan Michael.

The diastereoselective Pauson-Khand cyclization of nitrogen-oxygen, nitrogen-nitrogen tethered enynes and progress towards the synthesis of the axinellamines.

紀錄類型:	書目-電子資源 : Monograph/item
正題名/作者:	The diastereoselective Pauson-Khand cyclization of nitrogen-oxygen, nitrogen-nitrogen tethered enynes and progress towards the synthesis of the axinellamines.
作者:	Miller, Stefan Michael.
面頁冊數:	339 p.
附註:	Director: David Joseph Austin.
附註:	Source: Dissertation Abstracts International, Volume: 66-11, Section: B, page: 5987.
Contained By:	Dissertation Abstracts International66-11B.
標題:	Chemistry, Organic.
電子資源:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3194689
ISBN:	9780542394911

The diastereoselective Pauson-Khand cyclization of nitrogen-oxygen, nitrogen-nitrogen tethered enynes and progress towards the synthesis of the axinellamines.
Miller, Stefan Michael.

The diastereoselective Pauson-Khand cyclization of nitrogen-oxygen, nitrogen-nitrogen tethered enynes and progress towards the synthesis of the axinellamines. - 339 p.

Director: David Joseph Austin.

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

The Pauson-Khand cyclization is performed on transiently N-O or N-N tethered enyne systems yielding bicyclic cyclopentenones in a diastereoselective manner with the core structural features of several bisguanidine alkaloids including the palau'amines, styloguanidines, and axinellamines. Enynes containing a stereodefined allylic group are readily formed from the chiral synthon D-Mannitol and promotion of the cyclization reaction is achieved with an improved TMANO (trimethylamine N-oxide), NMO (N-methyl morpholine), or alkyl-sulfide/DMSO promoted induction sequence. A methodological study of numerous promotion conditions is provided detailing the effects of alternate promoters, solvent, temperature, and atmosphere on variously substituted N-O and N-N enynes. Furthermore, we demonstrate the ability of protection at the N-O, N-N site to promote the Pauson-Khand cyclization on unstrained disubstituted olefins. Ensuing cleavage of the tether provides a cyclopentane core with pendant orthogonally reactive functionality for further modification. In addition, the asymmetric Pauson-Khand is utilized for formation of the core ring of axinellamine absent a chiral auxillary, providing product in good yield with moderate enantioselectivities. Model systems are described for utilizing the asymmetric Pauson-Khand cyclization for the expedient synthesis of the axinellamines.

ISBN: 9780542394911Subjects--Topical Terms:

193634
Chemistry, Organic.

The diastereoselective Pauson-Khand cyclization of nitrogen-oxygen, nitrogen-nitrogen tethered enynes and progress towards the synthesis of the axinellamines.
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