Synthesis of lupiwighteone via a para-Claisen-Cope rearrangement

Nawaf Al-Maharik; Nigel Peter Botting

doi:10.1016/S0040-4020(03)00579-9

Synthesis of lupiwighteone via a para-Claisen-Cope rearrangement

Nawaf Al-Maharik, Nigel Peter Botting

Research output: Contribution to journal › Article › peer-review

Abstract

The lanthanide catalysed para-Claisen-Cope rearrangement has been used as the key step in a short synthesis of the prenylated isoflavone, lupiwighteone. The Mitsunobu reaction was employed for the 5-O-prenylation of the acid/base sensitive acetylated isoflavone to afford the allyl aryl ether precursor, which was then rearranged under mild conditions in good yield. Rearrangement of the isoflavone gave the 8-prenylisoflavone as a single product, in good yield. (C) 2003 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	4177-4181
Number of pages	5
Journal	Tetrahedron
Volume	59
Issue number	23
DOIs	https://doi.org/10.1016/S0040-4020(03)00579-9
Publication status	Published - 2 Jun 2003

Keywords

lupiwighteone
Claisen-Cope rearrangement
Mitsunobu reaction
ISOFLAVONOIDS
PHYTOESTROGENS
FLAVONES
LUPIN

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10.1016/S0040-4020(03)00579-9

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title = "Synthesis of lupiwighteone via a para-Claisen-Cope rearrangement",

abstract = "The lanthanide catalysed para-Claisen-Cope rearrangement has been used as the key step in a short synthesis of the prenylated isoflavone, lupiwighteone. The Mitsunobu reaction was employed for the 5-O-prenylation of the acid/base sensitive acetylated isoflavone to afford the allyl aryl ether precursor, which was then rearranged under mild conditions in good yield. Rearrangement of the isoflavone gave the 8-prenylisoflavone as a single product, in good yield. (C) 2003 Elsevier Science Ltd. All rights reserved.",

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T1 - Synthesis of lupiwighteone via a para-Claisen-Cope rearrangement

AU - Al-Maharik, Nawaf

AU - Botting, Nigel Peter

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N2 - The lanthanide catalysed para-Claisen-Cope rearrangement has been used as the key step in a short synthesis of the prenylated isoflavone, lupiwighteone. The Mitsunobu reaction was employed for the 5-O-prenylation of the acid/base sensitive acetylated isoflavone to afford the allyl aryl ether precursor, which was then rearranged under mild conditions in good yield. Rearrangement of the isoflavone gave the 8-prenylisoflavone as a single product, in good yield. (C) 2003 Elsevier Science Ltd. All rights reserved.

AB - The lanthanide catalysed para-Claisen-Cope rearrangement has been used as the key step in a short synthesis of the prenylated isoflavone, lupiwighteone. The Mitsunobu reaction was employed for the 5-O-prenylation of the acid/base sensitive acetylated isoflavone to afford the allyl aryl ether precursor, which was then rearranged under mild conditions in good yield. Rearrangement of the isoflavone gave the 8-prenylisoflavone as a single product, in good yield. (C) 2003 Elsevier Science Ltd. All rights reserved.

KW - lupiwighteone

KW - Claisen-Cope rearrangement

KW - Mitsunobu reaction

KW - ISOFLAVONOIDS

KW - PHYTOESTROGENS

KW - FLAVONES

KW - LUPIN

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DO - 10.1016/S0040-4020(03)00579-9

M3 - Article

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VL - 59

SP - 4177

EP - 4181

JO - Tetrahedron

JF - Tetrahedron

IS - 23

ER -

Synthesis of lupiwighteone via a para-Claisen-Cope rearrangement

Abstract

Keywords

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