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An Efficient Synthesis of (±)-Dehaloperophoramidine

Hoang, Anita LU ; Popov, Kirill LU and Somfai, Peter LU (2017) In Journal of Organic Chemistry 82(4). p.2171-2176
Abstract

Perophoramidine and communesin F are structurally related indole alkaloids with an intriguing polycyclic core containing vicinal all-carbon quaternary stereocenters. Dehaloperophoramidine is a dehalogenated synthetic analogue of perophoramidine. Synthetic studies toward the total synthesis of dehaloperophoramidine have led to the discovery of two novel domino processes, the first encompassing four steps and resulting in the formation of an ortho-amide. A thorough study of the reactivity of the ortho-amide functionality revealed the second domino reaction and ultimately yielded the target molecule. The vicinal all-carbon quaternary stereocenters having trans relative stereochemistry are constructed early in the reaction sequence by... (More)

Perophoramidine and communesin F are structurally related indole alkaloids with an intriguing polycyclic core containing vicinal all-carbon quaternary stereocenters. Dehaloperophoramidine is a dehalogenated synthetic analogue of perophoramidine. Synthetic studies toward the total synthesis of dehaloperophoramidine have led to the discovery of two novel domino processes, the first encompassing four steps and resulting in the formation of an ortho-amide. A thorough study of the reactivity of the ortho-amide functionality revealed the second domino reaction and ultimately yielded the target molecule. The vicinal all-carbon quaternary stereocenters having trans relative stereochemistry are constructed early in the reaction sequence by employing Overman's samarium mediated reductive dialkylation procedure. Described are the synthetic studies that led to the final eight-step synthesis of dehaloperophoramidine.

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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Organic Chemistry
volume
82
issue
4
pages
6 pages
publisher
The American Chemical Society
external identifiers
  • scopus:85013214695
  • wos:000394736000035
ISSN
0022-3263
DOI
10.1021/acs.joc.6b02969
language
English
LU publication?
yes
id
2f5a74fb-be93-4089-aed2-db42e2fd3ec8
date added to LUP
2017-03-01 09:41:10
date last changed
2018-03-04 04:59:36
@article{2f5a74fb-be93-4089-aed2-db42e2fd3ec8,
  abstract     = {<p>Perophoramidine and communesin F are structurally related indole alkaloids with an intriguing polycyclic core containing vicinal all-carbon quaternary stereocenters. Dehaloperophoramidine is a dehalogenated synthetic analogue of perophoramidine. Synthetic studies toward the total synthesis of dehaloperophoramidine have led to the discovery of two novel domino processes, the first encompassing four steps and resulting in the formation of an ortho-amide. A thorough study of the reactivity of the ortho-amide functionality revealed the second domino reaction and ultimately yielded the target molecule. The vicinal all-carbon quaternary stereocenters having trans relative stereochemistry are constructed early in the reaction sequence by employing Overman's samarium mediated reductive dialkylation procedure. Described are the synthetic studies that led to the final eight-step synthesis of dehaloperophoramidine.</p>},
  author       = {Hoang, Anita and Popov, Kirill and Somfai, Peter},
  issn         = {0022-3263},
  language     = {eng},
  month        = {02},
  number       = {4},
  pages        = {2171--2176},
  publisher    = {The American Chemical Society},
  series       = {Journal of Organic Chemistry},
  title        = {An Efficient Synthesis of (±)-Dehaloperophoramidine},
  url          = {http://dx.doi.org/10.1021/acs.joc.6b02969},
  volume       = {82},
  year         = {2017},
}