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Total synthesis of oasomycin A.

Harvard University.

Total synthesis of oasomycin A.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Total synthesis of oasomycin A.
Author:	Nagorny, Pavel.
Description:	262 p.
Notes:	Source: Dissertation Abstracts International, Volume: 68-02, Section: B, page: 0981.
Contained By:	Dissertation Abstracts International68-02B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3251301

Total synthesis of oasomycin A.
Nagorny, Pavel.

Total synthesis of oasomycin A. - 262 p.

Source: Dissertation Abstracts International, Volume: 68-02, Section: B, page: 0981.

Thesis (Ph.D.)--Harvard University, 2007.

*Please refer to dissertation for diagram.Subjects--Topical Terms:

193634
Chemistry, Organic.

Total synthesis of oasomycin A.
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005 20080111103838.5
008 090528s2007 eng d
035 $a 00311780
040 $a UMI $c UMI
100 0 $a Nagorny, Pavel. $3 264336
245 1 0 $a Total synthesis of oasomycin A.
300 $a 262 p.
500 $a Source: Dissertation Abstracts International, Volume: 68-02, Section: B, page: 0981.
502 $a Thesis (Ph.D.)--Harvard University, 2007.
520 # $a *Please refer to dissertation for diagram.
520 # $a The NMR-based structural assignment of the absolute and relative stereochemistry was confirmed by comparison of natural oasomycin A to the sample obtained by synthesis described herein.*
520 # $a The total synthesis of the macrolide oasomycin A is described. The convergent synthesis strategy divided this macrolide into five main fragments. These fragments were synthesized via aldol-based methodology and coupled. Key fragment couplings included an anti-Felkin selective aldol addition to construct the C28--C29 bond, Kociensky-Julia olefinations to construct the Delta12 and Delta38 olefins, and a competitive Weinreb amide acylation reaction to fashion the C21 --C22 bond. The utility of 4,5-diphenyloxazole as a carboxy surrogate has been demonstrated throughout the synthesis. The results of a systematic investigation of the late-stage macrolactonization that generated the 42-membered macrocycle of oasomycin A are also presented.
590 $a School code: 0084.
650 # 0 $a Chemistry, Organic. $3 193634
690 $a 0490
710 0 # $a Harvard University. $3 212445
773 0 # $g 68-02B. $t Dissertation Abstracts International
790 $a 0084
791 $a Ph.D.
792 $a 2007
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