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Indole diterpenoid synthetic studies...
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Davulcu, Akin H.
Indole diterpenoid synthetic studies: The total synthesis of (+)-nodulisporic acid F and studies toward the total synthesis of (-)-nodulisporic acid D.
Record Type:
Electronic resources : Monograph/item
Title/Author:
Indole diterpenoid synthetic studies: The total synthesis of (+)-nodulisporic acid F and studies toward the total synthesis of (-)-nodulisporic acid D.
Author:
Davulcu, Akin H.
Description:
308 p.
Notes:
Adviser: Amos B. Smith, III.
Notes:
Source: Dissertation Abstracts International, Volume: 67-06, Section: B, page: 3134.
Contained By:
Dissertation Abstracts International67-06B.
Subject:
Chemistry, Organic.
Online resource:
http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3223349
ISBN:
9780542738777
Indole diterpenoid synthetic studies: The total synthesis of (+)-nodulisporic acid F and studies toward the total synthesis of (-)-nodulisporic acid D.
Davulcu, Akin H.
Indole diterpenoid synthetic studies: The total synthesis of (+)-nodulisporic acid F and studies toward the total synthesis of (-)-nodulisporic acid D.
- 308 p.
Adviser: Amos B. Smith, III.
Thesis (Ph.D.)--University of Pennsylvania, 2006.
*Please refer to dissertation for diagrams.
ISBN: 9780542738777Subjects--Topical Terms:
193634
Chemistry, Organic.
Indole diterpenoid synthetic studies: The total synthesis of (+)-nodulisporic acid F and studies toward the total synthesis of (-)-nodulisporic acid D.
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Indole diterpenoid synthetic studies: The total synthesis of (+)-nodulisporic acid F and studies toward the total synthesis of (-)-nodulisporic acid D.
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308 p.
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Adviser: Amos B. Smith, III.
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Source: Dissertation Abstracts International, Volume: 67-06, Section: B, page: 3134.
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Thesis (Ph.D.)--University of Pennsylvania, 2006.
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*Please refer to dissertation for diagrams.
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Chapter one of this dissertation provides a general introduction to the indole diterpenoid class of natural products, with an emphasis on the recently discovered nodulisporic acids. Chapter two describes the stereocontrolled total synthesis of (+)-nodulisporic acid F. Highlights of the modular synthetic strategy include an efficient anionic coupling via the Smith 2-substituted indole synthesis, an optimized C-ring annulation protocol, and a late-stage installation of the alpha,beta-unsaturated carboxylic acid sidechain via the B-alkyl Suzuki-Miyaura cross-coupling reaction.*
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Chapter three details our overall strategy for the convergent, asymmetric total synthesis of (-)-nodulisporic acid D, a representative member of a recently nodulisporane class of architecturally complex indole alkaloids. In addition, we describe an expedient, stereocontrolled preparation of tricyclic western hemisphere subtarget (-)-104. Successful union of (-)- 104 with eastern hemisphere subtarget (-)-125 via our 2-substituted indole synthesis has enabled construction of the heptacyclic core of (-)-nodulisporic acid D.*
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http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3223349
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