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The reaction of hyperforin with hydride reducing agents.

Verotta, Luisella; Sterner, Olov LU ; Appendino, Giovanni; Bombardelli, Ezio and Pilati, Tullio (2006) In European Journal of Organic Chemistry p.5479-5484
Abstract
As part of a study aimed at generating analogues of hyperforin (1), the reaction of this prenylated phloroglucinol with various hydride reducing agents was investigated. Hyperforin contains two beta-dicarbonyl systems, one of which is non-enolizable, and it was interesting to assess the relative reactivity of these structural elements in the highly compact framework of the natural product. Depending on the reducing agent employed, a surprising range of compounds could be obtained, sometimes in synthetically useful yields. The stereochemistry of the LiAlH4-reduced product was secured by X-ray analysis and served as a base for elucidating the configuration of a series of reduced and deoxygenated analogues obtained with other reducing agents.... (More)
As part of a study aimed at generating analogues of hyperforin (1), the reaction of this prenylated phloroglucinol with various hydride reducing agents was investigated. Hyperforin contains two beta-dicarbonyl systems, one of which is non-enolizable, and it was interesting to assess the relative reactivity of these structural elements in the highly compact framework of the natural product. Depending on the reducing agent employed, a surprising range of compounds could be obtained, sometimes in synthetically useful yields. The stereochemistry of the LiAlH4-reduced product was secured by X-ray analysis and served as a base for elucidating the configuration of a series of reduced and deoxygenated analogues obtained with other reducing agents. The chemoselectivity observed in these reactions is apparently the result of a combination of metal-chelation and hydrogen-bonding effects. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
acylphloroglucinols, natural products, reduction
in
European Journal of Organic Chemistry
pages
5479 - 5484
publisher
John Wiley & Sons
external identifiers
  • wos:000243078000008
  • scopus:33845932899
ISSN
1434-193X
DOI
10.1002/ejoc.200600644
language
English
LU publication?
yes
id
99b01d1c-d4d3-4f98-b12d-34d2096af052 (old id 781868)
date added to LUP
2008-01-04 16:01:56
date last changed
2017-06-18 04:49:28
@article{99b01d1c-d4d3-4f98-b12d-34d2096af052,
  abstract     = {As part of a study aimed at generating analogues of hyperforin (1), the reaction of this prenylated phloroglucinol with various hydride reducing agents was investigated. Hyperforin contains two beta-dicarbonyl systems, one of which is non-enolizable, and it was interesting to assess the relative reactivity of these structural elements in the highly compact framework of the natural product. Depending on the reducing agent employed, a surprising range of compounds could be obtained, sometimes in synthetically useful yields. The stereochemistry of the LiAlH4-reduced product was secured by X-ray analysis and served as a base for elucidating the configuration of a series of reduced and deoxygenated analogues obtained with other reducing agents. The chemoselectivity observed in these reactions is apparently the result of a combination of metal-chelation and hydrogen-bonding effects.},
  author       = {Verotta, Luisella and Sterner, Olov and Appendino, Giovanni and Bombardelli, Ezio and Pilati, Tullio},
  issn         = {1434-193X},
  keyword      = {acylphloroglucinols,natural products,reduction},
  language     = {eng},
  pages        = {5479--5484},
  publisher    = {John Wiley & Sons},
  series       = {European Journal of Organic Chemistry},
  title        = {The reaction of hyperforin with hydride reducing agents.},
  url          = {http://dx.doi.org/10.1002/ejoc.200600644},
  year         = {2006},
}