First Lewis acid catalyzed [4+2] cycloaddition reaction of 1,3,3-trimethyl-2-vinyl-1-cyclohexene with chromones: a new entry to analogues of the puupehenone group of marine diterpenoids and kampanols

被引：4

作者：

Kamble, Rajesh M. ^{[1
]}

Ramana, M. M. V. ^{[1
]}

机构：

[1] Univ Bombay, Dept Chem, Bombay 400098, Maharashtra, India

来源：

MONATSHEFTE FUR CHEMIE | 2011年 / 142卷 / 05期

关键词：

Cycloaddition; Chromones; Lewis acid; Regioselectivity; Stereoselectivity; Terpenoids; DIELS-ALDER REACTIONS; ELECTRON-RICH DIENES; NATURAL-PRODUCTS; ORDER VERONGIDA; SPONGE; METABOLITES; QUINONES; 1,3,3-TRIMETHYL-2-VINYLCYCLOHEXENE; DERIVATIVES; HYRTIOS;

D O I：

10.1007/s00706-011-0480-z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A rapid assembly of the tetracyclic core of marine diterpenoids related to puupehenone and kampanols featuring a Lewis acid catalyzed [4+2] cycloaddition reaction of 1,3,3-trimethyl-2-vinyl-1-cyclohexene and chromone dienophiles is described.

引用

页码：501 / 506

页数：6

共 11 条

[1] First Lewis acid catalyzed [4+2] cycloaddition reaction of 1,3,3-trimethyl-2-vinyl-1-cyclohexene with chromones: a new entry to analogues of the puupehenone group of marine diterpenoids and kampanols
Rajesh M. Kamble
M. M. V. Ramana
Monatshefte für Chemie - Chemical Monthly, 2011, 142 : 501 - 506
[2] Microwave-assisted Diels-Alder reaction of 1,3,3-trimethyl-2-vinyl-1-cyclohexene with chromones - An expeditious approach to analogues of the puupehenone group of marine diterpenoids and kampanols
Kamble, Rajesh M.
Ramana, M. M. V.
CANADIAN JOURNAL OF CHEMISTRY, 2010, 88 (12) : 1233 - 1239
[3] Diels-Alder Reaction of 2-Ethenyl-1,3,3-trimethylcyclohexene with 4H-Chromen-4-ones: A Convergent Approach to ABCD Tetracyclic Core of Marine Diterpenoids Related to Puupehenone and Kampanols
Kamble, Rajesh M.
Ramana, M. M. V.
HELVETICA CHIMICA ACTA, 2011, 94 (02) : 261 - 267
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Sergeev, Pavel G.
Novikov, Roman A.
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Huang, Qiwen
Li, Xinyao
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[8] Highly regioselective synthesis of 2,3-disubstituted 2H-1-benzopyrans: Bronsted acid catalyzed [4+2] cycloaddition reaction with a variety of arylalkynes via ortho-quinone methides
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[9] Exo/endo selectivity-control in Lewis-acid catalyzed tandem heterocyclization/formal [4+3] cycloaddition: synthesis of polyheterocycles from 2-(1-alkynyl)-2-alken-1-ones and 1,3-diphenylisobenzofuran
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[10] Lewis Acid Catalyzed Diels-Alder Reactions of (E)-1-Methyl-2-styrylquinolin-4(1H)-ones with ortho-Benzoquinodimethane: Synthesis of New 2-(3-Arylnaphthalen-2-yl)-1-methylquinolin-4(1H)-ones
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