The reaction of hyperforin with hydride reducing agents.
(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)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/781868
- author
- Verotta, Luisella ; Sterner, Olov LU ; Appendino, Giovanni ; Bombardelli, Ezio and Pilati, Tullio
- organization
- publishing date
- 2006
- 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 Inc.
- external identifiers
-
- wos:000243078000008
- scopus:33845932899
- ISSN
- 1434-193X
- DOI
- 10.1002/ejoc.200600644
- language
- English
- LU publication?
- yes
- additional info
- The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
- id
- 99b01d1c-d4d3-4f98-b12d-34d2096af052 (old id 781868)
- date added to LUP
- 2016-04-04 12:07:16
- date last changed
- 2022-01-29 22:58:01
@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}},
keywords = {{acylphloroglucinols; natural products; reduction}},
language = {{eng}},
pages = {{5479--5484}},
publisher = {{John Wiley & Sons Inc.}},
series = {{European Journal of Organic Chemistry}},
title = {{The reaction of hyperforin with hydride reducing agents.}},
url = {{http://dx.doi.org/10.1002/ejoc.200600644}},
doi = {{10.1002/ejoc.200600644}},
year = {{2006}},
}