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The total synthesis of Ustiloxin D.

Record Type:	Electronic resources : Monograph/item
Title/Author:	The total synthesis of Ustiloxin D.
Author:	Tanaka, Hiroko.
Description:	203 p.
Notes:	Adviser: Thomas J. Wandless.
Notes:	Source: Dissertation Abstracts International, Volume: 64-03, Section: B, page: 1253.
Contained By:	Dissertation Abstracts International64-03B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3085233
ISBN:	0496330403

The total synthesis of Ustiloxin D.
Tanaka, Hiroko.

The total synthesis of Ustiloxin D. [electronic resource] - 203 p.

Adviser: Thomas J. Wandless.

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

*Please refer to dissertation for diagrams.

ISBN: 0496330403Subjects--Topical Terms:

193634
Chemistry, Organic.

The total synthesis of Ustiloxin D.
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100 0 $a Tanaka, Hiroko. $3 226992
245 1 4 $a The total synthesis of Ustiloxin D. $h [electronic resource]
300 $a 203 p.
500 $a Adviser: Thomas J. Wandless.
500 $a Source: Dissertation Abstracts International, Volume: 64-03, Section: B, page: 1253.
502 $a Thesis (Ph.D.)--Stanford University, 2003.
520 # $a *Please refer to dissertation for diagrams.
520 # $a Overall, our Ustiloxin D synthesis consisted of a longest linear sequence of 20 steps and a total yield of 3.2% for C2-epi-Ustiloxin D and 2.6% for Ustiloxin D.
520 # $a Starting from 3,4-dihydroxybenzaldehyde, we have completed the total synthesis of the natural product Ustiloxin D. The key steps in the synthesis include the following reactions: (1) Chiral aluminum complex-catalyzed Aldol reaction between an aromatic oxazole and a benzaldehyde derivative to set the C9 and C10 stereochemistry. (2) Chiral pi-allyl palladium reaction with a phenol to synthesize the chiral tertiary alkyl-aryl ether linkage, setting C2 stereochemistry. (3) Asymmetric dihydroxylation reaction to set the C3 stereochemistry. (4) Macrolactamization at the N7-C8 junction using PyAOP in DMF. Other unique features of our synthesis include the use of the oxazoline generated in the Aldol reaction as a protecting group for the N-methylaminoalcohol moiety, and incorporation of the glycine side chain prior to macrocyclization. The use of the oxazoline allowed us to eliminate multiple protection and deprotection steps and incorporation of the side chain at an earlier stage allows us to extend this synthesis to the synthesis of the more complex Phomopsin B.
520 # $a Ustiloxins A-D and Phomopsin A and B are antimitotic agents exerting toxicity through induction of microtubule depolymerization. The Ustiloxins were isolated from the aqueous extract of the fungus Ustilaginoidea virens produced on rice panicles, whereas the Phomopsins were isolated from Phomopsin leptostromiformis, a fungus infecting hay. From our interest in studying the mechanism of action of these antimitotic agents, we have decided to develop a route for the total synthesis of one of these compounds, Ustiloxin D.*
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790 1 0 $a Wandless, Thomas J., $e advisor
791 $a Ph.D.
792 $a 2003
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