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Novel utilization of transition meta...

Pfeiffer, Steven Shane.

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Novel utilization of transition metal organometallic chemistry for the synthesis of natural products.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Novel utilization of transition metal organometallic chemistry for the synthesis of natural products./
Author:	Pfeiffer, Steven Shane.
Description:	700 p.
Notes:	Source: Dissertation Abstracts International, Volume: 64-02, Section: B, page: 0720.
Contained By:	Dissertation Abstracts International64-02B.
Subject:	Chemistry, Organic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3079960

Novel utilization of transition metal organometallic chemistry for the synthesis of natural products.
Pfeiffer, Steven Shane.

Novel utilization of transition metal organometallic chemistry for the synthesis of natural products. - 700 p.

Source: Dissertation Abstracts International, Volume: 64-02, Section: B, page: 0720.

Thesis (Ph.D.)--University of California, Santa Barbara, 2003.

One of the most important transformations in synthetic organic chemistry is the formation of a C-C bond, including direct installation of the aldehyde functionality. A Weinreb-like formamide was developed as a formylating reagent towards various metallated nucleophiles, leading to aldehydes in good to excellent yields without detectable over addition products.Subjects--Topical Terms:

516206
Chemistry, Organic.

Novel utilization of transition metal organometallic chemistry for the synthesis of natural products.
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100 1 $a Pfeiffer, Steven Shane. $3 1949437
245 1 0 $a Novel utilization of transition metal organometallic chemistry for the synthesis of natural products.
300 $a 700 p.
500 $a Source: Dissertation Abstracts International, Volume: 64-02, Section: B, page: 0720.
500 $a Chair: Bruce H. Lipshutz.
502 $a Thesis (Ph.D.)--University of California, Santa Barbara, 2003.
520 $a One of the most important transformations in synthetic organic chemistry is the formation of a C-C bond, including direct installation of the aldehyde functionality. A Weinreb-like formamide was developed as a formylating reagent towards various metallated nucleophiles, leading to aldehydes in good to excellent yields without detectable over addition products.
520 $a The discovery of vancomycin, a highly potent antibiotic, by Eli Lilly in 1956, from soil samples collected in the jungles of Borneo, prompted synthetic studies of this glycopeptide by several research groups. In the late 1990's three total syntheses were reported, which succeeded in piecing together several amino acid residues consisting of 18 chiral centers along with stereocontrol of three internal elements of atropisomerism. However, in each case the AB-biaryl ring system, present in this natural product, had the undesired R -configuration as the major constituent. The use of chlorine atoms as protecting groups to lock the biaryl ring system into one conformation together with the Bringmann lactone method provided a model AB-biaryl ring system with the desired S-configuration. Separately, use of a chiral tether incorporated within an enediyne system was investigated and applied toward the vancomycin AB-biaryl system.
520 $a Transition metals have become necessary tools in organic synthesis. The use of heterogeneous nickel in metal-catalyzed reactions has advantages over its palladium counterpart due to cost, reactivity, and waste disposal. Ni(0), being more nucleophilic, is able to insert into a C-Cl bond under mild conditions allowing various reactions to occur. A system composed of a base, PPh 3, and dimethylamine-borane was developed as an effective method to reduce aryl chlorides, and to deprotect Cbz-protected heteroaromatic amines in the presence of sensitive functional groups.
520 $a Oftentimes labeled the "miracle nutrient", coenzyme Q 10 has been shown to mitigate against high-blood pressure, alleviate respiratory ailments, prevent the spread of cancer cells, enhance energy levels, and has been used medicinally since the 1960's. Starting with solanesol, a trisesquiterpene alcohol isolated from tobacco leaves, and a commercially available benzaldehyde derivative, a short, highly efficient synthesis of CoQ10 consisting of six linear steps in an overall yield of >64% was developed.
590 $a School code: 0035.
650 4 $a Chemistry, Organic. $3 516206
650 4 $a Chemistry, Pharmaceutical. $3 550957
690 $a 0490
690 $a 0491
710 2 0 $a University of California, Santa Barbara. $3 1017586
773 0 $t Dissertation Abstracts International $g 64-02B.
790 1 0 $a Lipshutz, Bruce H., $e advisor
790 $a 0035
791 $a Ph.D.
792 $a 2003
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3079960