An efficient synthesis of alpha-cuparenone

被引：15

作者：

Chavan, SP ^{[1
]}

Ravindranathan, T ^{[1
]}

Patil, SS ^{[1
]}

Dhondge, VD ^{[1
]}

Dantale, SW ^{[1
]}

机构：

[1] NATL CHEM LAB,DIV ORGAN CHEM TECHNOL,POONA 411008,MAHARASHTRA,INDIA

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 15期

关键词：

D O I：

10.1016/0040-4039(96)00345-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of alpha-Cuparenone is described. The key step involved are photorearrangement of alpha-halo aryl ketone (4) to 1-methyl-1-(p-tolyl)acetic acid (5) and extremely mild, essentially neutral, room temperature 13-aza-claisen reaction of N-allylamide (6). Copyright (C) 1996 Published by Elsevier Science Ltd

引用

页码：2629 / 2630

页数：2

共 7 条

[1] MG/MEOH MEDIATED INTRAMOLECULAR REDUCTIVE CYCLIZATION OF ACTIVATED DIENES [J].

CHAVAN, SP ;

ETHIRAJ, KS .

TETRAHEDRON LETTERS, 1995, 36 (13) :2281-2284

[2]

PETER E, 1985, CHEM BER, V118, P825

[3] PHOTOCHEMICAL-REARRANGEMENT OF ALPHA-CHLORO-PROPIOPHENONES TO ALPHA-ARYLPROPANOIC ACIDS - STUDIES ON CHIRALITY TRANSFER AND SYNTHESIS OF (S)-(+)-IBUPROFEN AND (S)-(+)-KETOPROFEN [J].

SONAWANE, HR ;

BELLUR, NS ;

KULKARNI, DG ;

AYYANGAR, NR .

TETRAHEDRON, 1994, 50 (04) :1243-1260

[4]

SUKH D, 1964, TETRAHEDRON LETT, P73

[5]

TOSHIO H, 1993, TETRAHEDRON-ASYMMETR, V4, P21

[6] AN EXTREMELY MILD 3-AZA-CLAISEN REACTION .2. NEW CONDITIONS AND THE REARRANGEMENT OF ALPHA-HETEROATOM SUBSTITUTED AMIDES [J].

WALTERS, MA ;

HOEM, AB ;

ARCAND, HR ;

HEGEMAN, AD ;

MCDONOUGH, CS .

TETRAHEDRON LETTERS, 1993, 34 (09) :1453-1456

[7] OXY-CYCLOPROPANES IN ORGANOCHEMICAL SYNTHESIS - TOTAL SYNTHESES OF (+/-)-ALPHA-CUPARENONE AND (+/-)-BETA-VETIVONE [J].

WENKERT, E ;

BUCKWALTER, BL ;

CRAVEIRO, AA ;

SANCHEZ, EL ;

SATHE, SS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (04) :1267-1273

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