A regiodivergent synthesis of ring A C-prenylflavones

Alberto Minassi; Anna Giana; Abdellah Ech-Chahad; Giovanni Appendino

doi:10.1021/ol800665w

A regiodivergent synthesis of ring A C-prenylflavones

Alberto Minassi, Anna Giana, Abdellah Ech-Chahad, Giovanni Appendino

Dipartimento di Scienze del Farmaco

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

Abstract

(Chemical Equation Presented) Capitalizing on the use of orthogonal protecting groups and the development of a modified Robinson flavone synthesis that avoids harsh acidic conditions, a regioselective synthesis of 6- and 8-prenylflavones from the same prenylated disilylated phloracetophenone (9) has been developed, targeting cannflavin B (1d), the COX-inhibiting principle of marijuana, and its unnatural isomer isocannflavin B (1e) as model compounds.

Lingua originale	Inglese
pagine (da-a)	2267-2270
Numero di pagine	4
Rivista	Organic Letters
Volume	10
Numero di pubblicazione	11
DOI	https://doi.org/10.1021/ol800665w
Stato di pubblicazione	Pubblicato - 5 giu 2008

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10.1021/ol800665w

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title = "A regiodivergent synthesis of ring A C-prenylflavones",

abstract = "(Chemical Equation Presented) Capitalizing on the use of orthogonal protecting groups and the development of a modified Robinson flavone synthesis that avoids harsh acidic conditions, a regioselective synthesis of 6- and 8-prenylflavones from the same prenylated disilylated phloracetophenone (9) has been developed, targeting cannflavin B (1d), the COX-inhibiting principle of marijuana, and its unnatural isomer isocannflavin B (1e) as model compounds.",

author = "Alberto Minassi and Anna Giana and Abdellah Ech-Chahad and Giovanni Appendino",

year = "2008",

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AU - Giana, Anna

AU - Ech-Chahad, Abdellah

AU - Appendino, Giovanni

PY - 2008/6/5

Y1 - 2008/6/5

N2 - (Chemical Equation Presented) Capitalizing on the use of orthogonal protecting groups and the development of a modified Robinson flavone synthesis that avoids harsh acidic conditions, a regioselective synthesis of 6- and 8-prenylflavones from the same prenylated disilylated phloracetophenone (9) has been developed, targeting cannflavin B (1d), the COX-inhibiting principle of marijuana, and its unnatural isomer isocannflavin B (1e) as model compounds.

AB - (Chemical Equation Presented) Capitalizing on the use of orthogonal protecting groups and the development of a modified Robinson flavone synthesis that avoids harsh acidic conditions, a regioselective synthesis of 6- and 8-prenylflavones from the same prenylated disilylated phloracetophenone (9) has been developed, targeting cannflavin B (1d), the COX-inhibiting principle of marijuana, and its unnatural isomer isocannflavin B (1e) as model compounds.

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DO - 10.1021/ol800665w

M3 - Article

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A regiodivergent synthesis of ring A C-prenylflavones

Abstract

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