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Progress toward the total synthesis of diazonamide A

Record Type:	Electronic resources : Monograph/item
Title/Author:	Progress toward the total synthesis of diazonamide A
Author:	Fuerst, Douglas Edward.
Description:	257 p.
Notes:	Director: John Louis Wood.
Notes:	Source: Dissertation Abstracts International, Volume: 64-11, Section: B, page: 5526.
Contained By:	Dissertation Abstracts International64-11B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3111478
ISBN:	0496590081

Progress toward the total synthesis of diazonamide A
Fuerst, Douglas Edward.

Progress toward the total synthesis of diazonamide A [electronic resource] - 257 p.

Director: John Louis Wood.

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

Diazonamide A (3) was isolated in 1991 from the colonial ascidian Diazona angulata and has been shown to be a potent cytotoxin with IC50 values of less than 15 ng/mL against HCT-116 human colon carcinoma and B-16 murine melanoma cancer cell lines. Due to its unique structure and promising biological activity, 3 has led to a Herculean effort by the synthetic community in recent years. Reported herein is a novel approach to this the new class of natural products.

ISBN: 0496590081Subjects--Topical Terms:

193634
Chemistry, Organic.

Progress toward the total synthesis of diazonamide A
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245 1 0 $a Progress toward the total synthesis of diazonamide A $h [electronic resource]
300 $a 257 p.
500 $a Director: John Louis Wood.
500 $a Source: Dissertation Abstracts International, Volume: 64-11, Section: B, page: 5526.
502 $a Thesis (Ph.D.)--Yale University, 2003.
520 # $a Diazonamide A (3) was isolated in 1991 from the colonial ascidian Diazona angulata and has been shown to be a potent cytotoxin with IC50 values of less than 15 ng/mL against HCT-116 human colon carcinoma and B-16 murine melanoma cancer cell lines. Due to its unique structure and promising biological activity, 3 has led to a Herculean effort by the synthetic community in recent years. Reported herein is a novel approach to this the new class of natural products.
520 # $a In efforts directed toward fully functional diazonamide A, an efficient synthesis of benzofuranone 198 was developed utilizing a robust pi-allyl alkylation/Eu(fod)3 catalyzed Claisen rearrangement sequence ( 198 → 210). Alkylation of 198 with indole 262 affords advanced intermediate 275, which is for advancement to diazonamide A (3).
520 # $a Work in a model system has led to the development of two complementary approaches to the diazonamide bisaryl quaternary center C(10). The first approach involves the asymmetric cyclopropanation and subsequent ring opening of benzofuran 195. The second strategy relies upon a more concise alkylation route ideal for material advancement (198 → 210).
590 $a School code: 0265.
650 # 0 $a Chemistry, Organic. $3 193634
650 # 0 $a Chemistry, Pharmaceutical. $3 206042
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710 0 # $a Yale University. $3 212430
773 0 # $g 64-11B. $t Dissertation Abstracts International
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790 1 0 $a Wood, John Louis, $e advisor
791 $a Ph.D.
792 $a 2003
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