Use of an acetylenic sulfone as an alkene dipole equivalent in the synthesis of (+/-)-pumiliotoxin C

被引：18

作者：

Back, TG

Nakajima, K

机构：

[1] Department of Chemistry, University of Calgary, Calgary

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 06期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/S0040-4039(96)02506-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cycloaddition of methyl cis-2-amino-trans-6-methylcyclohexanecarboxylate (3) with 1-p-(toluenesulfonyl)-1-pentyne (4) afforded the corresponding enaminone 2, that was in turn reduced to (+/-)-pumiliotoxin C (1). The acetylenic sulfone 4 thus functions as the synthetic equivalent of the alkene dipole 5 in this process. (C) 1997, Elsevier Science Ltd.

引用

页码：989 / 992

页数：4

共 40 条

[1] A SYNTHESIS OF DL-PUMILIOTOXIN-C
ABE, K
TSUGOSHI, T
NAKAMURA, N
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (11) : 3351 - 3352
[2] BACK TG, 1995, TETRAHEDRON LETT, V36, P4737
[3] SELENOSULFONATION OF ACETYLENES - PREPARATION OF NOVEL BETA-(PHENYLSELENO)VINYL SULFONES AND THEIR CONVERSION TO ACETYLENIC AND BETA-FUNCTIONALIZED SULFONES
BACK, TG
COLLINS, S
KERR, RG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (18) : 3077 - 3084
[4] SELENOSULFONATION OF DISUBSTITUTED ACETYLENES - REACTIONS OF CORRESPONDING VINYL SELENOXIDES AND ANOMALOUS FORMATION OF A KETENE DISELENOACETAL
BACK, TG
COLLINS, S
GOKHALE, U
LAW, KW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (24) : 4776 - 4779
[5] REACTIONS OF AMINES WITH BETA-(PHENYLSELENINYL)VINYL SULFONES DERIVED FROM THE SELENOSULFONATION OF ACETYLENES - FORMATION OF ENAMINE SULFONES
BACK, TG
COLLINS, S
LAW, KW
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1985, 63 (08): : 2313 - 2318
[6] ASYMMETRIC-SYNTHESIS .8. BIOGENETICALLY PATTERNED APPROACH TO THE CHIRAL TOTAL SYNTHESIS OF (-)-PUMILIOTOXIN-C
BONIN, M
ROYER, J
GRIERSON, DS
HUSSON, HP
[J]. TETRAHEDRON LETTERS, 1986, 27 (14) : 1569 - 1572
[7] THE ISOXAZOLINE-5-SPIROCYCLOPROPANE ROUTE TO (+/-)-PUMILIOTOXIN-C
BRANDI, A
CORDERO, FM
GOTI, A
GUARNA, A
[J]. TETRAHEDRON LETTERS, 1992, 33 (44) : 6697 - 6700
[8] STEREOSPECIFIC SYNTHESIS OF 1,3-OXAZOLIDINES FROM ALLENIC AND ACETYLENIC SULFONES
CINQUINI, M
COZZI, F
PELOSI, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (06): : 1430 - 1432
[9] A SHORT, ASYMMETRIC-SYNTHESIS OF (-)-PUMILIOTOXIN-C
COMINS, DL
DEHGHANI, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (24) : 1838 - 1839
[10] N-ACYLDIHYDROPYRIDONES AS SYNTHETIC INTERMEDIATES - A SHORT SYNTHESIS OF (+/-)-PUMILIOTOXIN-C
COMINS, DL
DEHGHANI, A
[J]. TETRAHEDRON LETTERS, 1991, 32 (41) : 5697 - 5700

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