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The total synthesis of kalihinol C and related natural products.

Record Type:	Electronic resources : Monograph/item
Title/Author:	The total synthesis of kalihinol C and related natural products.
Author:	White, Ryan D.
Description:	364 p.
Notes:	Director: John Louis Wood.
Notes:	Source: Dissertation Abstracts International, Volume: 64-10, Section: B, page: 4953.
Contained By:	Dissertation Abstracts International64-10B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3109483
ISBN:	0496570250

The total synthesis of kalihinol C and related natural products.
White, Ryan D.

The total synthesis of kalihinol C and related natural products. [electronic resource] - 364 p.

Director: John Louis Wood.

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

Based in part on extensive model system studies which culminated in the total syntheses of (+/-)-10-isocyano-4-cadinene (15) and (+/-)-10-isothiocyanato-4-cadinene (16), efforts directed toward kalihinol A led to the first total syntheses of (+/-)-kalihinol C (42) and (+/-)-epi-C(14)-kalihinol C (185). The successful synthetic strategy utilized a series of substrate-controlled, diastereoselective reactions in which a conformationally rigid decalin core was used to dictate introduction of the requisite functionality. The synthetic sequence was highlighted by a diastereoselective (i) IMDA cycloaddition of 109, (ii) epoxidation of cis-decalin 110, (iii) azindination of olefin 45, and (iv) anti-Felkin propiolate addition to methyl ketone 141. Future efforts will focus upon the advancement of 155 to kalihinol A and related kalihinols.

ISBN: 0496570250Subjects--Topical Terms:

193634
Chemistry, Organic.

The total synthesis of kalihinol C and related natural products.
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245 1 4 $a The total synthesis of kalihinol C and related natural products. $h [electronic resource]
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500 $a Director: John Louis Wood.
500 $a Source: Dissertation Abstracts International, Volume: 64-10, Section: B, page: 4953.
502 $a Thesis (Ph.D.)--Yale University, 2003.
520 # $a Based in part on extensive model system studies which culminated in the total syntheses of (+/-)-10-isocyano-4-cadinene (15) and (+/-)-10-isothiocyanato-4-cadinene (16), efforts directed toward kalihinol A led to the first total syntheses of (+/-)-kalihinol C (42) and (+/-)-epi-C(14)-kalihinol C (185). The successful synthetic strategy utilized a series of substrate-controlled, diastereoselective reactions in which a conformationally rigid decalin core was used to dictate introduction of the requisite functionality. The synthetic sequence was highlighted by a diastereoselective (i) IMDA cycloaddition of 109, (ii) epoxidation of cis-decalin 110, (iii) azindination of olefin 45, and (iv) anti-Felkin propiolate addition to methyl ketone 141. Future efforts will focus upon the advancement of 155 to kalihinol A and related kalihinols.
520 # $a Kalihinol A (1) was isolated in 1984 from the marine sponge Acanthella cavernosa. The structure and isolation of nearly forty additional natural products related to kalihinol A were later described and shown to possess a variety of biological activities. In particular, kalihinol A was shown to exhibit potent antimalarial activity against P. falciparum . Reported herein is a multi-faceted strategy for the total synthesis of kalihinol A and related natural products.
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