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

Record Type:	Language materials, manuscript : Monograph/item
Title/Author:	Towards the Total Synthesis of the Xiamycin Family of Indolosesquiterpenes :/
Reminder of title:	Synthesis Of Oridamycins A and B.
Author:	Trotta, Adam Howell.
Description:	1 online resource (312 pages)
Notes:	Source: Dissertation Abstracts International, Volume: 79-03(E), Section: B.
Contained By:	Dissertation Abstracts International79-03B(E).
Subject:	Organic chemistry. -
Online resource:	click for full text (PQDT)
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. - 1 online resource (312 pages)

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

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

Includes bibliographical references

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.

Electronic reproduction.
Ann Arbor, Mich. :
ProQuest,
2018

Mode of access: World Wide Web

ISBN: 9780355501872Subjects--Topical Terms:

1148722
Organic chemistry.
Index Terms--Genre/Form:

554714
Electronic books.

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 1191988
245 1 0 $a Towards the Total Synthesis of the Xiamycin Family of Indolosesquiterpenes : $b Synthesis Of Oridamycins A and B.
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300 $a 1 online resource (312 pages)
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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.
504 $a Includes bibliographical references
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.
533 $a Electronic reproduction. $b Ann Arbor, Mich. : $c ProQuest, $d 2018
538 $a Mode of access: World Wide Web
650 4 $a Organic chemistry. $3 1148722
650 4 $a Chemistry. $3 593913
655 7 $a Electronic books. $2 local $3 554714
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690 $a 0485
710 2 $a ProQuest Information and Learning Co. $3 1178819
710 2 $a Weill Medical College of Cornell University. $b Chemical Biology. $3 1191989
773 0 $t Dissertation Abstracts International $g 79-03B(E).
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10635024 $z click for full text (PQDT)