eprintid: 18743
rev_number: 16
userid: 1419
dir: disk0/00/01/87/43
datestamp: 2013-05-28 15:24:10
lastmod: 2019-02-02 15:57:16
status_changed: 2013-05-28 15:24:10
type: article
metadata_visibility: show
item_issues_count: 0
eprint_status: archive
creators_name: Hoye, AT
creators_name: Wipf, P
creators_email: 
creators_email: pwipf@pitt.edu
creators_id: 
creators_id: PWIPF
title: Total synthesis of (-)-sessilifoliamide C and (-)-8-epi-stemoamide
ispublished: pub
divisions: sch_as_chemistry
full_text_status: public
abstract: 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.
date: 2011-05-20
date_type: published
publication: Organic Letters
volume: 13
number: 10
pagerange: 2634 - 2637
refereed: TRUE
issn: 1523-7060
id_number: 10.1021/ol200743u
other_id: NLM NIHMS291055
other_id: NLM PMC3099051
pmcid: PMC3099051
pmid: 21510628
mesh_headings: Alkaloids--chemical synthesis
mesh_headings: Alkaloids--chemistry
mesh_headings: Heterocyclic Compounds, 3-Ring--chemical synthesis
mesh_headings: Heterocyclic Compounds, 3-Ring--chemistry
mesh_headings: Molecular Structure
mesh_headings: Stemonaceae--chemistry
mesh_headings: Stereoisomerism
chemical_names: Alkaloids
chemical_names: Heterocyclic Compounds, 3-Ring
chemical_names: sessilifoliamide C
chemical_names: stemoamide
citation:   Hoye, AT and Wipf, P  (2011) Total synthesis of (-)-sessilifoliamide C and (-)-8-epi-stemoamide.  Organic Letters, 13 (10).  2634 - 2637.  ISSN 1523-7060     
document_url: http://d-scholarship-dev.library.pitt.edu/18743/1/licence.txt