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Part I. Total synthesis of (-)-cylindrocyclophane A :Exploring the reversible nature of the olefin cross-metathesis reaction. Part II. Total synthesis of (+)-13-deoxytedanolide and progress toward the total synthesis of tedanolide.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Part I. Total synthesis of (-)-cylindrocyclophane A :
Reminder of title:	Exploring the reversible nature of the olefin cross-metathesis reaction. Part II. Total synthesis of (+)-13-deoxytedanolide and progress toward the total synthesis of tedanolide.
Author:	Adams, Christopher Michael.
Description:	529 p.
Notes:	Source: Dissertation Abstracts International, Volume: 64-06, Section: B, page: 2669.
Notes:	Supervisor: Amos B. Smith, III.
Contained By:	Dissertation Abstracts International64-06B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3095852
ISBN:	0496434772

Part I. Total synthesis of (-)-cylindrocyclophane A :Exploring the reversible nature of the olefin cross-metathesis reaction. Part II. Total synthesis of (+)-13-deoxytedanolide and progress toward the total synthesis of tedanolide.
Adams, Christopher Michael.

Part I. Total synthesis of (-)-cylindrocyclophane A :Exploring the reversible nature of the olefin cross-metathesis reaction. Part II. Total synthesis of (+)-13-deoxytedanolide and progress toward the total synthesis of tedanolide. [electronic resource] - 529 p.

Source: Dissertation Abstracts International, Volume: 64-06, Section: B, page: 2669.

Thesis (Ph.D.)--University of Pennsylvania, 2003.

*Please refer to dissertation for diagrams.

ISBN: 0496434772Subjects--Topical Terms:

193634
Chemistry, Organic.

Part I. Total synthesis of (-)-cylindrocyclophane A :Exploring the reversible nature of the olefin cross-metathesis reaction. Part II. Total synthesis of (+)-13-deoxytedanolide and progress toward the total synthesis of tedanolide.
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245 1 0 $a Part I. Total synthesis of (-)-cylindrocyclophane A : $b Exploring the reversible nature of the olefin cross-metathesis reaction. Part II. Total synthesis of (+)-13-deoxytedanolide and progress toward the total synthesis of tedanolide. $h [electronic resource]
300 $a 529 p.
500 $a Source: Dissertation Abstracts International, Volume: 64-06, Section: B, page: 2669.
500 $a Supervisor: Amos B. Smith, III.
502 $a Thesis (Ph.D.)--University of Pennsylvania, 2003.
520 # $a *Please refer to dissertation for diagrams.
520 # $a Chapter three of Part II describes the construction of the carbon skeletons of (+)-tedanolide and (+)-13-deoxytedanolide via union of the elaborated linchpin with the requisite epoxide and iodide fragments.*
520 # $a In addition, this chapter details the development of a novel oxidation strategy, which employs the Evans-Tishchenko reaction to access the seco-acid of (+)-13-deoxytedanolide, and ultimately leads to the completion of the first total synthesis of (+)-13-deoxytedanolide.*
520 # $a Part I, chapter one provides an introduction to the cylindrocyclophane family of natural products. Specifically, the isolation, structure elucidation, biosynthetic origin, and biological activity of the cylindrocyclophanes are discussed. Furthermore, relevant synthetic approaches toward the cylindrocyclophanes are delineated.*
520 # $a Part II of this dissertation discusses the first total synthesis of (+)-13-deoxytedanolide and efforts toward (+)-tedanolide. Chapter one introduces the tedanolide family and details the isolation, structural elucidation, and impressive biological activity of (+)-tedanolide and (+)-13-deoxytedanolide. In addition, relevant synthetic approaches by other research groups toward the tedanolides are summarized.*
520 # $a Part II, chapter two introduces the synthetic strategy envisioned for the synthesis of the tedanolides. The synthetic plan entails a unified approach to both (+)-tedanolide and (+)-13-deoxytedanolide that calls for the late-stage introduction of the trisubstituted epoxide and employs a dithiane-vinyl iodide linchpin.*
520 # $a The final chapter of Part I explores the reversible nature of olefin metathesis as it pertains to the exclusive formation of the [7,7]-paracyclophane skeleton. Molecular modeling and experimental evidence support the theory that a cascade of reversible olefin metatheses drives the reaction to the [7,7]-paracyclophane skeleton.*
520 # $a The second chapter of Part I describes the total synthesis of (-)-cylindrocyclophane A via a cross olefin metathesis dimerization cascade. The dimerization substrate was accessed via Danheiser annulation, which employed a siloxyalkyne available from Kowalski homologation of the appropriate ester.*
520 # $a This two part dissertation describes the total syntheses of (-)-cylindrocyclophane A, a C2-symmetric naturally occurring [7,7]-paracyclophane, and (+)-13-deoxytedanolide, a potent antitumor marine macrolide.
590 $a School code: 0175.
650 # 0 $a Chemistry, Organic. $3 193634
710 0 # $a University of Pennsylvania. $3 212781
773 0 # $g 64-06B. $t Dissertation Abstracts International
790 $a 0175
790 1 0 $a Smith, Amos B., III, $e advisor
791 $a Ph.D.
792 $a 2003
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