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Progress toward the total synthesis ...

Fuerst, Douglas Edward.

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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:	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. - 257 p.

Source: Dissertation Abstracts International, Volume: 64-11, Section: B, page: 5526.

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:

516206
Chemistry, Organic.

Progress toward the total synthesis of diazonamide A.
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020 $a 0496590081
035 $a (UnM)AAI3111478
035 $a AAI3111478
040 $a UnM $c UnM
100 1 $a Fuerst, Douglas Edward. $3 1932299
245 1 0 $a Progress toward the total synthesis of diazonamide A.
300 $a 257 p.
500 $a Source: Dissertation Abstracts International, Volume: 64-11, Section: B, page: 5526.
500 $a Director: John Louis Wood.
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 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).
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).
590 $a School code: 0265.
650 4 $a Chemistry, Organic. $3 516206
650 4 $a Chemistry, Pharmaceutical. $3 550957
690 $a 0490
690 $a 0491
710 2 0 $a Yale University. $3 515640
773 0 $t Dissertation Abstracts International $g 64-11B.
790 1 0 $a Wood, John Louis, $e advisor
790 $a 0265
791 $a Ph.D.
792 $a 2003
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3111478