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I. Samarium(II) iodide mediated intr...

St. Jean, David Joseph, Jr.

I. Samarium(II) iodide mediated intramolecular conjugate addition reactions of alpha, beta-unsaturated lactones. II. The total synthesis of deacetoxyalcyonin acetate using a Lewis acid mediated [4+3] annulation.

Record Type:	Electronic resources : Monograph/item
Title/Author:	I. Samarium(II) iodide mediated intramolecular conjugate addition reactions of alpha, beta-unsaturated lactones. II. The total synthesis of deacetoxyalcyonin acetate using a Lewis acid mediated [4+3] annulation.
Author:	St. Jean, David Joseph, Jr.
Description:	564 p.
Notes:	Source: Dissertation Abstracts International, Volume: 65-06, Section: B, page: 2941.
Notes:	Supervisor: Gary A. Molander.
Contained By:	Dissertation Abstracts International65-06B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3138077
ISBN:	0496852477

I. Samarium(II) iodide mediated intramolecular conjugate addition reactions of alpha, beta-unsaturated lactones. II. The total synthesis of deacetoxyalcyonin acetate using a Lewis acid mediated [4+3] annulation.
St. Jean, David Joseph, Jr.

I. Samarium(II) iodide mediated intramolecular conjugate addition reactions of alpha, beta-unsaturated lactones. II. The total synthesis of deacetoxyalcyonin acetate using a Lewis acid mediated [4+3] annulation. - 564 p.

Source: Dissertation Abstracts International, Volume: 65-06, Section: B, page: 2941.

Thesis (Ph.D.)--University of Pennsylvania, 2004.

Samarium(II) iodide, in the presence of catalytic amounts of nickel(II) iodide, has been used to promote intramolecular conjugate additions of alkyl halides onto alpha,beta-unsaturated lactones. This process is applicable to a number of alpha,beta-unsaturated lactones, including tetrasubstituted olefins, and has been shown to be quite general for the formation of saturated bicyclic and tricyclic lactones. The method presented herein provides a mild, efficient process to form structurally complex lactones from simple precursors.

ISBN: 0496852477Subjects--Topical Terms:

193634
Chemistry, Organic.

I. Samarium(II) iodide mediated intramolecular conjugate addition reactions of alpha, beta-unsaturated lactones. II. The total synthesis of deacetoxyalcyonin acetate using a Lewis acid mediated [4+3] annulation.
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245 1 0 $a I. Samarium(II) iodide mediated intramolecular conjugate addition reactions of alpha, beta-unsaturated lactones. II. The total synthesis of deacetoxyalcyonin acetate using a Lewis acid mediated [4+3] annulation.
300 $a 564 p.
500 $a Source: Dissertation Abstracts International, Volume: 65-06, Section: B, page: 2941.
500 $a Supervisor: Gary A. Molander.
502 $a Thesis (Ph.D.)--University of Pennsylvania, 2004.
520 # $a Samarium(II) iodide, in the presence of catalytic amounts of nickel(II) iodide, has been used to promote intramolecular conjugate additions of alkyl halides onto alpha,beta-unsaturated lactones. This process is applicable to a number of alpha,beta-unsaturated lactones, including tetrasubstituted olefins, and has been shown to be quite general for the formation of saturated bicyclic and tricyclic lactones. The method presented herein provides a mild, efficient process to form structurally complex lactones from simple precursors.
520 # $a The Molander approach relied on a Lewis acid mediated [4+3] annulation to construct the key hexahydroisobenzofuran moiety present in deacetoxyalcyonin acetate. Using this annulation, we constructed the core of deacetoxyalcyonin acetate in only three steps from alpha-phallendrene. The product of this annulation was then carried on to complete the total synthesis in only 17 steps. Additionally, the final product of this synthetic route was unambiguously confirmed by X-ray crystallographic analysis. The total synthesis of deacetoxyalcyonin acetate not only constitutes the shortest known route to this molecule but also provides a potential platform for the synthesis of other biologically active eunicellin diterpenes.
520 # $a The eunicellin diterpenes are a class of natural products that display a broad range of biological activity. Along with this biological importance, the unique structure of these natural products has made them attractive targets for the synthetic community. Since the isolation of eunicellin by Djerassi and co-workers more than 35 years ago, a number of total syntheses have been reported. The contributions of these research groups are discussed below. The first molecule from this class to succumb to total synthesis was deacetoxyalcyonin acetate; a eunicellin diterpene isolated from the Cladiella species of soft coral. This synthesis, reported by Prof. Larry Overman in 1995, successfully constructed the target structure in 25 steps. Later, this synthesis was refined to provide a more efficient (23 steps) route to deacetoxyalcyonin acetate as well as other eunicellin diterpenes.
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790 1 0 $a Molander, Gary A., $e advisor
791 $a Ph.D.
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