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Towards the Total Synthesis of the X...

Trotta, Adam Howell.

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Towards the Total Synthesis of the Xiamycin Family of Indolosesquiterpenes: Synthesis Of Oridamycins A and B.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Towards the Total Synthesis of the Xiamycin Family of Indolosesquiterpenes: Synthesis Of Oridamycins A and B./
Author:	Trotta, Adam Howell.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2018,
Description:	312 p.
Notes:	Source: Dissertation Abstracts International, Volume: 79-03(E), Section: B.
Contained By:	Dissertation Abstracts International79-03B(E).
Subject:	Organic chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10635024
ISBN:	9780355501872

Towards the Total Synthesis of the Xiamycin Family of Indolosesquiterpenes: Synthesis Of Oridamycins A and B.
Trotta, Adam Howell.

Towards the Total Synthesis of the Xiamycin Family of Indolosesquiterpenes: Synthesis Of Oridamycins A and B. - Ann Arbor : ProQuest Dissertations & Theses, 2018 - 312 p.

Source: Dissertation Abstracts International, Volume: 79-03(E), Section: B.

Thesis (Ph.D.)--Weill Medical College of Cornell University, 2018.

The xiamycin family of indolosesquiterpenes comprises bioactive compounds isolated from several strains of Streptomyces. Several dimeric family members have shown strong activity against several strains of bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin resistant Enterococcus (VRE). These promising initial results, coupled with the limited production of these compounds from their natural sources, prompted the design of a unified synthetic strategy capable of producing several family members from a common synthetic intermediate.

ISBN: 9780355501872Subjects--Topical Terms:

523952
Organic chemistry.

Towards the Total Synthesis of the Xiamycin Family of Indolosesquiterpenes: Synthesis Of Oridamycins A and B.
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100 1 $a Trotta, Adam Howell. $3 3351311
245 1 0 $a Towards the Total Synthesis of the Xiamycin Family of Indolosesquiterpenes: Synthesis Of Oridamycins A and B.
260 1 $a Ann Arbor : $b ProQuest Dissertations & Theses, $c 2018
300 $a 312 p.
500 $a Source: Dissertation Abstracts International, Volume: 79-03(E), Section: B.
500 $a Advisers: Samuel J. Danishefsky; Derek S. Tan.
502 $a Thesis (Ph.D.)--Weill Medical College of Cornell University, 2018.
520 $a The xiamycin family of indolosesquiterpenes comprises bioactive compounds isolated from several strains of Streptomyces. Several dimeric family members have shown strong activity against several strains of bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin resistant Enterococcus (VRE). These promising initial results, coupled with the limited production of these compounds from their natural sources, prompted the design of a unified synthetic strategy capable of producing several family members from a common synthetic intermediate.
520 $a Structurally, the xiamycin family members consist of a carbazole fused to a trans-decalin ring system. The difference between xiamycin A and oridamycin A is a single epimeric stereocenter at C16. It was envisioned that a key oxidative radical cyclization could produce both stereochemical patterns---with free-radical conditions generating the stereochemistry associated with oridamycin A, and chelated radical conditions producing the stereochemistry corresponding to xiamycin A.
520 $a The total synthesis of oridamycins A and B was completed, utilizing a free-radical cyclization that correctly set three contiguous stereocenters, including two quaternary carbons. The fused carbazole was produced using a 6?-electrocyclization/aromatization sequence. Finally, oridamycin B was accessed through a palladium-catalyzed, oxime-directed C-H oxidation.
590 $a School code: 0967.
650 4 $a Organic chemistry. $3 523952
650 4 $a Chemistry. $3 516420
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