Oxidative fragmentation of the bridged β-triketone core of hyperforin

Luisella Verotta; Erminio Lovaglio; Olov Sterner; Giovanni Appendino; Ezio Bombardelli

doi:10.1002/ejoc.200300568

Oxidative fragmentation of the bridged β-triketone core of hyperforin

Luisella Verotta
, Erminio Lovaglio
, Olov Sterner
, Giovanni Appendino
, Ezio Bombardelli

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

Abstract

The β-triketone core of the antidepressant phloroglucinol hyperforin (1) undergoes a series of peroxide-induced oxidative rearrangements leading to compound 5, which is formed by opening of ring A, and compound 6, which is formed by removal of the C-1 carbonyl bridge. A mechanistic rationale for this process is proposed.

Lingua originale	Inglese
pagine (da-a)	1193-1197
Numero di pagine	5
Rivista	European Journal of Organic Chemistry
Numero di pubblicazione	6
DOI	https://doi.org/10.1002/ejoc.200300568
Stato di pubblicazione	Pubblicato - 12 mar 2004
Pubblicato esternamente	Sì

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10.1002/ejoc.200300568

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title = "Oxidative fragmentation of the bridged β-triketone core of hyperforin",

abstract = "The β-triketone core of the antidepressant phloroglucinol hyperforin (1) undergoes a series of peroxide-induced oxidative rearrangements leading to compound 5, which is formed by opening of ring A, and compound 6, which is formed by removal of the C-1 carbonyl bridge. A mechanistic rationale for this process is proposed.",

keywords = "Acylphloroglucinols, Fragmentation, Hypericum perforatum, Natural products, Rearrangement, Terpenoids",

author = "Luisella Verotta and Erminio Lovaglio and Olov Sterner and Giovanni Appendino and Ezio Bombardelli",

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AU - Verotta, Luisella

AU - Lovaglio, Erminio

AU - Sterner, Olov

AU - Appendino, Giovanni

AU - Bombardelli, Ezio

PY - 2004/3/12

Y1 - 2004/3/12

N2 - The β-triketone core of the antidepressant phloroglucinol hyperforin (1) undergoes a series of peroxide-induced oxidative rearrangements leading to compound 5, which is formed by opening of ring A, and compound 6, which is formed by removal of the C-1 carbonyl bridge. A mechanistic rationale for this process is proposed.

AB - The β-triketone core of the antidepressant phloroglucinol hyperforin (1) undergoes a series of peroxide-induced oxidative rearrangements leading to compound 5, which is formed by opening of ring A, and compound 6, which is formed by removal of the C-1 carbonyl bridge. A mechanistic rationale for this process is proposed.

KW - Acylphloroglucinols

KW - Fragmentation

KW - Hypericum perforatum

KW - Natural products

KW - Rearrangement

KW - Terpenoids

UR - https://www.scopus.com/pages/publications/4544345612

U2 - 10.1002/ejoc.200300568

DO - 10.1002/ejoc.200300568

M3 - Article

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SP - 1193

EP - 1197

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 6

ER -

Oxidative fragmentation of the bridged β-triketone core of hyperforin

Abstract

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