DIELS-ALDER REACTIONS OF CYCLOALKENONES .22. HIGH PRESSURE-LEWIS ACID-CATALYZED DIELS-ALDER REACTIONS OF 3-METHYLCYCLOHEX-2-EN-1-ONE - A STRAIGHTFORWARD ROUTE TO CIS AND TRANS ANGULARLY METHYLATED OCTALONES

被引：22

作者：

ABEN, RWM

MINUTI, L

SCHERREN, HW

TATICCHI, A

机构：

[1] UNIV PERUGIA,DIPARTMENTO CHIM,VIA ELCE SOTTO 8,I-06100 PERUGIA,ITALY

[2] CATHOLIC UNIV NIJMEGEN,DEPT ORGAN CHEM,6525 ED NIJMEGEN,NETHERLANDS

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 44期

关键词：

D O I：

10.1016/0040-4039(91)80191-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By the application of high pressure in combination with EtAlCl2 as the Lewis acid, it is possible to achieve Diels-Alder reactions of 3-methylcyclohex-2-en-1-one with simple acyclic dienes. This cycloaddition offers the most straightforward route to cis and trans angularly methylated octalones, precursors in the total synthesis of terpenes and steroids.

引用

页码：6445 / 6448

页数：4

共 14 条

[1] ABEN RW, UNPUB
[2] HIGH-PRESSURE-PROMOTED (2 + 2) CYCLOADDITIONS OF IMINES WITH ELECTRON-RICH ALKENES - A SIMPLE ROUTE TO AZETIDINES AND BETA-AMINO CARBONYL-COMPOUNDS
ABEN, RWM
SMIT, R
SCHEEREN, JW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (03) : 365 - 370
[3] DIELS-ALDER REACTIONS OF CYCLOALKENONES .15. SYNTHESIS OF CIS-DELTA-6-4A-METHYL-1-OCTALONES AND TRANS-DELTA-6-4A-METHYL-1-OCTALONES
ANGELL, EC
FRINGUELLI, F
PIZZO, F
MINUTI, L
TATICCHI, A
WENKERT, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (05) : 1217 - 1218
[4] A NEW GENERAL SYNTHETIC APPROACH TO DITERPENES - APPLICATION TO SYNTHESES OF (+/-)-TAXODIONE AND (+/-)-ROYLEANONE
ENGLER, TA
SAMPATH, U
NAGANATHAN, S
VELDE, DV
TAKUSAGAWA, F
YOHANNES, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (24) : 5712 - 5727
[5] DIELS-ALDER REACTIONS OF CYCLOALKENONES .16. ENDO DIASTEREOSELECTIVITY OF SOME CYCLOALKENONES IN REACTIONS WITH 1,3-CYCLOHEXADIENE
FRINGUELLI, F
GUO, M
MINUTI, L
PIZZO, F
TATICCHI, A
WENKERT, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (03) : 710 - 712
[6] DIELS-ALDER REACTIONS OF CYCLOALKENONES .3. EFFECTS OF SPECIFIC REACTION PARAMETERS
FRINGUELLI, F
PIZZO, F
TATICCHI, A
WENKERT, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (17) : 2802 - 2808
[7] DIELS-ALDER REACTIONS OF CYCLOALKENONES .1. PREPARATION AND STRUCTURE OF THE ADDUCTS
FRINGUELLI, F
PIZZO, F
TATICCHI, A
HALLS, TDJ
WENKERT, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (26) : 5056 - 5065
[8] DIELS-ALDER REACTIONS OF CYCLOALKENONES IN ORGANIC-SYNTHESIS - A REVIEW
FRINGUELLI, F
TATICCHI, A
WENKERT, E
[J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1990, 22 (02) : 131 - 165
[9] BIOMIMETIC POLYENE CYCLIZATIONS - ASYMMETRIC INDUCTION IN CYCLIZATION OF A DIENIC ACETAL
JOHNSON, WS
HARBERT, CA
RATCLIFFE, BE
STIPANOVIC, RD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (20) : 6188 - 6193
[10] DIELS-ALDER REACTIONS INVOLVING CROSS-CONJUGATED DIENONES - EFFECTS OF SUBSTITUTION ON REACTIVITY
LIOTTA, D
SAINDANE, M
BARNUM, C
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) : 3224 - 3226

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