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Total synthesis of (-)-sessilifoliamide C and (-)-8-epi-stemoamide

Hoye, AT and Wipf, P (2011) Total synthesis of (-)-sessilifoliamide C and (-)-8-epi-stemoamide. Organic Letters, 13 (10). 2634 - 2637. ISSN 1523-7060

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A convergent route featuring [3,3]-sigmatropic rearrangements of a linchpin azepinopyrrolidine served to install two of the four contiguous stereocenters present in the tricyclic Stemona alkaloids sessilifoliamide and stemoamide. In addition to the first total synthesis of (-)-sessilifoliamide C, a potential biosynthetic relationship between the sessilifoliamides and previously reported Stemona alkaloids is presented. © 2011 American Chemical Society.


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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Hoye, AT
Wipf, Ppwipf@pitt.eduPWIPF
Date: 20 May 2011
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 13
Number: 10
Page Range: 2634 - 2637
DOI or Unique Handle: 10.1021/ol200743u
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
MeSH Headings: Alkaloids--chemical synthesis; Alkaloids--chemistry; Heterocyclic Compounds, 3-Ring--chemical synthesis; Heterocyclic Compounds, 3-Ring--chemistry; Molecular Structure; Stemonaceae--chemistry; Stereoisomerism
Other ID: NLM NIHMS291055, NLM PMC3099051
PubMed Central ID: PMC3099051
PubMed ID: 21510628
Date Deposited: 28 May 2013 15:24
Last Modified: 02 Feb 2019 15:57


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