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Total synthesis of (+)- and (-)-salicylihalamides A and related analogs. Studies towards the total synthesis of (+)-peloruside A.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Total synthesis of (+)- and (-)-salicylihalamides A and related analogs. Studies towards the total synthesis of (+)-peloruside A.
Author:	Zheng, Junying.
Description:	533 p.
Notes:	Source: Dissertation Abstracts International, Volume: 64-10, Section: B, page: 4955.
Notes:	Supervisor: Amos B. Smith, III.
Contained By:	Dissertation Abstracts International64-10B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3109242
ISBN:	0496567853

Total synthesis of (+)- and (-)-salicylihalamides A and related analogs. Studies towards the total synthesis of (+)-peloruside A.
Zheng, Junying.

Total synthesis of (+)- and (-)-salicylihalamides A and related analogs. Studies towards the total synthesis of (+)-peloruside A. [electronic resource] - 533 p.

Source: Dissertation Abstracts International, Volume: 64-10, Section: B, page: 4955.

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

*Please refer to dissertation for diagrams.

ISBN: 0496567853Subjects--Topical Terms:

193634
Chemistry, Organic.

Total synthesis of (+)- and (-)-salicylihalamides A and related analogs. Studies towards the total synthesis of (+)-peloruside A.
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245 1 0 $a Total synthesis of (+)- and (-)-salicylihalamides A and related analogs. Studies towards the total synthesis of (+)-peloruside A. $h [electronic resource]
300 $a 533 p.
500 $a Source: Dissertation Abstracts International, Volume: 64-10, Section: B, page: 4955.
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 Key features of the synthetic strategy include: (1) A highly E-selective ring-closing metathesis to construct the 12-membered salicylihalamide A macrocycle; and (2) A practical method for installation of the labile ene-hepta-(Z,Z)-dienamide side chain, involving N-acylation of enecarbamate (-)- 80, the latter derived from the corresponding alpha,beta unsaturated carboxylic acid (+)-25, via acyl azide formation and thermal Curtius rearrangement.*
520 # $a Peloruside A (145) is a novel cytotoxic polyketide, isolated from marine sponge Mycale hentscheli. Retrosynthetic disconnection of peloruside A (145) suggested two subtargets aldehyde 263 and methylketone 262. Further disconnection of methylketone led to dithiane 264 and epoxide 208.*
520 # $a Synthetic studies comprise the following cornerstone strategies: (1) Construction of C(1)--C(12) carbon skeleton via coupling of dithiane (-)-264 with epoxide (-)-208; (2) Setting the stereochemistry at C(5) via a highly stereoselective reduction of ketone (-)-269 with K-selectride in toluene (dr = 8:1), and (3) Union of C(1)--C(12) methylketone (-)-262 with C(13)--C(24) aldehyde (+)-263 via Mukaiyama aldol coupling.*
520 # $a The first part of this dissertation describes the total synthesis of (+)- and (-)-salicylihalamide A (1) and their analogs (chapter one, chapter two and chapter three). Isolated from marine sponge of the genus Haliclona, salicylihalamide A displays potent cytotoxicity against human tumor cell lines and possesses a unique mode of action. Retrosynthetic disconnection of salicylihalamide A led to three fragment alcohol 82, carboxylic acid 9 and acid chloride 79.*
520 # $a The second part of this dissertation describes studies directed towards the total synthesis of (-)-peloruside A 145 (Chapter Four and Chapter Five).
520 # $a Two structurally simplified analogs (116 and 117) were also prepared, which displayed significant, but attenuated cell growth inhibitory activity against several human tumor cell lines.*
520 # $a Unfortunately, attempts to close the macrocycle via Mitsunobu macrocyclization were unsuccessful. Due to the lack of material, no further progress could be obtained.*
590 $a School code: 0175.
650 # 0 $a Chemistry, Organic. $3 193634
710 0 # $a University of Pennsylvania. $3 212781
773 0 # $g 64-10B. $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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