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Studies toward the total synthesis of cochleamycin A.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Studies toward the total synthesis of cochleamycin A.
Author:	Goodman, Krista Beaver.
Description:	143 p.
Notes:	Adviser: David A. Evans.
Notes:	Source: Dissertation Abstracts International, Volume: 64-01, Section: B, page: 0212.
Contained By:	Dissertation Abstracts International64-01B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3076885
ISBN:	0493973478

Studies toward the total synthesis of cochleamycin A.
Goodman, Krista Beaver.

Studies toward the total synthesis of cochleamycin A. [electronic resource] - 143 p.

Adviser: David A. Evans.

Thesis (Ph.D.)--Harvard University, 2003.

*Please refer to dissertation for diagrams.

ISBN: 0493973478Subjects--Topical Terms:

193634
Chemistry, Organic.

Studies toward the total synthesis of cochleamycin A.
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100 $a Goodman, Krista Beaver. $3 226914
245 1 0 $a Studies toward the total synthesis of cochleamycin A. $h [electronic resource]
300 $a 143 p.
500 $a Adviser: David A. Evans.
500 $a Source: Dissertation Abstracts International, Volume: 64-01, Section: B, page: 0212.
502 $a Thesis (Ph.D.)--Harvard University, 2003.
520 $a *Please refer to dissertation for diagrams.
520 $a A modified ester-derived tetraene was synthesized in 20 steps and 6% overall yield. Thermolysis of this intermediate induced a highly selective Diels-Alder reaction to generate a single diastereomeric product. Although this product possessed the undesired C4--C5 alkylidene geometry, it contained the correct A-B-C ring system of 1, and represents the complete carbon skeleton of the cochleamycins. However, elaboration of this Diels-Alder adduct to cochleamycin A has not been achieved to date.
520 $a A synthetic approach to cochleamycin A based on a biomimetic transannular Diels-Alder reaction is described. The synthesis of a macrocyclic lactone tetraene was accomplished in 22 steps and 4% overall yield. Key steps in the synthesis include a Suzuki cross-coupling reaction, a pi-allylpalladium macrocyclization, and a selenoxide elimination. Upon thermolysis, this intermediate irreversibly isomerized to a macrocyclic 2H-pyran, which did not undergo a transannular Diels-Alder reaction.*
590 $a School code: 0084.
650 $a Chemistry, Organic. $3 193634
710 $a Harvard University. $3 212445
773 0 $g 64-01B. $t Dissertation Abstracts International
790 $a 0084
790 1 0 $a Evans, David A., $e advisor
791 $a Ph.D.
792 $a 2003
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3076885 $z http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3076885