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Asymmetric syntheses of pectenotoxins -4 and -8.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Asymmetric syntheses of pectenotoxins -4 and -8.
Author:	Rajapakse, Hemaka Anthony.
Description:	211 p.
Notes:	Source: Dissertation Abstracts International, Volume: 64-01, Section: B, page: 0217.
Contained By:	Dissertation Abstracts International64-01B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3076909
ISBN:	0493975888

Asymmetric syntheses of pectenotoxins -4 and -8.
Rajapakse, Hemaka Anthony.

Asymmetric syntheses of pectenotoxins -4 and -8. [electronic resource] - 211 p.

Source: Dissertation Abstracts International, Volume: 64-01, Section: B, page: 0217.

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

*Please refer to dissertation for diagrams.

ISBN: 0493975888Subjects--Topical Terms:

193634
Chemistry, Organic.

Asymmetric syntheses of pectenotoxins -4 and -8.
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520 # $a *Please refer to dissertation for diagrams.
520 # $a The total synthesis of pectenotoxin-4 has been achieved in 37 linear steps from commercially available material and 0.3% overall yield. The chiral building blocks for the synthesis were derived from catalytic enantioselective reactions, chiral auxiliary based chemistry, D-mannitol, and lactic acid. Felkin-controlled addition to aldehydes, chelate-controlled reduction of ketones, directed epoxidation of olefins, and iodoetherification reactions were used to internally relay stereochemistry and access the highly oxygenated structure of the pectenotoxins. Key bond constructions include a metalloenamine-epoxide alkylation, late stage olefination, and macrocyclization. The use of the N-phenylamide as a carboxyl surrogate, and the utility of the previously unused tert-butoxydiphenylsilyl ether protective group in a multistep synthesis is also described. Synthetic pectenotoxin-4 was isomerized to pectenotoxin-8 upon exposure to mild acid.*
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