Abstract/Details

I. Total synthesis of stemonine. II. Studies towards the total synthesis of kendomycin


2006 2006

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Abstract (summary)

Enantioselective total synthesis of (-)-stemonine was achieved via a convergent assembly of acyclic precursors. Key transformations include a Staudinger-aza-Wittig reaction to form the central perhydroazepine ring system and an Iodine-induced tandem cyclization to construct the pyrolidino-butyrolactome framework.

The synthesis of an advanced intermediate leading towards (-)-kendomycin is described. The synthetic scheme features the application of the asymmetric conjugate addition methodology for the early generation of C13-C14 ( E)-trisubstituted olefin, providing an efficient assembly of the ansa chain. Condensation reactions probed the Julia olefination and ortho-directed metallation for attachment of the aromatic system.

Indexing (details)


Subject
Organic chemistry
Classification
0490: Organic chemistry
Identifier / keyword
Pure sciences; Kendomycin; Stemonine
Title
I. Total synthesis of stemonine. II. Studies towards the total synthesis of kendomycin
Author
Shamim, Khalida
Number of pages
215
Publication year
2006
Degree date
2006
School code
0093
Source
DAI-B 67/12, Dissertation Abstracts International
Place of publication
Ann Arbor
Country of publication
United States
Advisor
Williams, David R.
University/institution
Indiana University
University location
United States -- Indiana
Degree
Ph.D.
Source type
Dissertations & Theses
Language
English
Document type
Dissertation/Thesis
Dissertation/thesis number
3243781
ProQuest document ID
305336849
Copyright
Database copyright ProQuest LLC; ProQuest does not claim copyright in the individual underlying works.
Document URL
http://search.proquest.com/docview/305336849
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