CHIRAL SYNTHONS FROM CARVONE .4. RADICAL CYCLIZATION STRATEGIES TO BRIDGED SYSTEMS - SYNTHESIS OF BICYCLO[3.2.1]OCTAN-3-ONES FROM (S)-CARVONE

被引：31

作者：

SRIKRISHNA, A

HEMAMALINI, P

机构：

[1] Department of Organic Chemistry, Indian Institute of Science

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 16期

关键词：

D O I：

10.1021/jo00303a023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Radical cyclization of the bromo enones 2a-e, obtained by regiospecific bromoetherification reaction on the electron-rich double bond of (S)-carvone (1), furnished regio- and stereospecifically bicyclo[3.2.1]octan-3-ones 3a-e and 4a-e. Analogously, radical cyclizations of the alcohols 6 and 7 gave bicyclo[3.2.1]octan-3-ols 8 and 9, and the bromo enones 11a,b gave the bridgehead-substituted bicyclo[3.2.1]octan-3-ones 12a,b and 13a,b. © 1990, American Chemical Society. All rights reserved.

引用

页码：4883 / 4887

页数：5

共 32 条

[1] Synthesis of highly functionalised enantiopure bicyclo[3.2.1]-octane systems from carvone
Abad, A
Agulló, C
Cuñat, AC
de Alfonso, I
Navarro, I
Vera, N
MOLECULES, 2004, 9 (05): : 287 - 299
[2] Chiral synthons from carvone .22. Synthesis of chiral bicyclo[2.2.2]octa-5,7-dien-2-ones
Srikrishna, A
Danieldoss, S
Sharma, GVR
SYNTHETIC COMMUNICATIONS, 1997, 27 (04) : 601 - 608
[3] CHIRAL SYNTHONS FROM CARVONE .11. A REGIOSPECIFIC RADICAL ANNULATION STRATEGY TO FUNCTIONALIZED CHIRAL BICYCLO[3.3.1]NONANES
SRIKRISHNA, A
HEMAMALINI, P
VENKATESWARLU, S
TETRAHEDRON, 1994, 50 (29) : 8781 - 8792
[4] RADICAL CYCLIZATION OF DIENES .4. ENANTIOMERICALLY PURE BUILDING-BLOCKS FROM (R)-(-)-CARVONE AND (S)-(+)-CARVONE FOR THE SYNTHESIS OF NATURALLY-OCCURRING TRIQUINANES
WEINGES, K
REICHERT, H
SYNLETT, 1991, (11) : 785 - 786
[5] Chiral synthons from carvone .24. Photochemical rearrangements of chiral bicyclo[2.2.2]oct-5-en-2-ones
Srikrishna, A
Danieldoss, S
SYNTHETIC COMMUNICATIONS, 1997, 27 (04) : 655 - 661
[6] REGIOSPECIFIC SYNTHESIS OF CHIRAL BICYCLO[2.2.2]OCT-5-EN-2-ONES FROM S-CARVONE
SRIKRISHNA, A
HEMAMALINI, P
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1990, 29 (03): : 201 - 202
[7] Chiral synthons from carvone, Part 56. Enantiospecific synthesis of (-)-4-thiocyanatoneopupukeanane
Srikrishna, A
Gharpure, SJ
ARKIVOC, 2002, : 52 - 62
[8] Chiral synthons from carvone: Part 41. Enantiospecific synthesis of (+)-3-valeranone and (+)-valerane
Srikrishna, A
Dinesh, C
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2000, 39 (05): : 323 - 325
[9] Chiral synthons from carvone .26. Synthesis of chiral bicyclo[3.3.1]nonanes via a tandem intermolecular alkylation-intramolecular Michael reaction sequence
Srikrishna, A
Reddy, TJ
Kumar, PP
SYNLETT, 1997, (06) : 663 - 664
[10] RADICAL-TYPE CYCLIZATION OF DIENES .6. TOTAL SYNTHESIS OF (-)-COROLIN AND (-)-EPICORIOLIN FROM (S)-(+)-CARVONE
WEINGES, K
BRAUN, R
HUBERPATZ, U
IRNGARTINGER, H
LIEBIGS ANNALEN DER CHEMIE, 1993, (10): : 1133 - 1140

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