A convenient asymmetric access to triquinanic compounds

被引：8

作者：

BintzGiudicelli, C

Weymann, O

Uguen, D

DeCian, A

Fischer, J

机构：

[1] ULP,ECPM,CNRS,ORGAN SYNTH LAB,F-67008 STRASBOURG,FRANCE

[2] ULP,CNRS,CRISTALLOCHIM LAB,F-67070 STRASBOURG,FRANCE

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 16期

关键词：

D O I：

10.1016/S0040-4039(97)00475-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thermal rearrangement of a propargylic sulfinate prepared from (R)-pulegone led, with an acceptable diastereoselectivity, to a spiro sulfone which could be transformed into dihydropentalenic acid, methyl ester. (C) 1997 Published by Elsevier Science Ltd.

引用

收藏

页码：2841 / 2844

页数：4

相关论文

共 14 条

[1] HIGHLY STEREOCONTROLLED AND REGIOCONTROLLED CYCLOPENTANNULATION VIA ALLYLPHOSPHONATE CONJUGATE ADDITION AND HYDROBORATION OXIDATION ELIMINATION - SYNTHESIS OF PENTALENIC ACID WITH VIRTUALLY COMPLETE STEREOCONTROL AND REGIOCONTROL [J].

AGNEL, G ;

NEGISHI, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7424-7426

[2]

BINTZ C, 1996, THESIS U L PASTEUR S

[3] INTRAMOLECULAR PHOTOCYCLOADDITIONS CYCLOBUTANE FRAGMENTATION - TOTAL SYNTHESIS OF (+/-)-PENTALENENE, (+/-)-PENTALENIC ACID, AND (+/-)-DEOXYPENTALENIC ACID [J].

CRIMMINS, MT ;

DELOACH, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (04) :800-806

[4] RHODIUM(I)-CATALYZED HYDROBORATION OF OLEFINS - THE DOCUMENTATION OF REGIOCHEMICAL AND STEREOCHEMICAL CONTROL IN CYCLIC AND ACYCLIC SYSTEMS [J].

EVANS, DA ;

FU, GC ;

HOVEYDA, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6917-6918

[5] SYSTEM ORIENTED DESIGN OF TRIQUINANES - STEREOCONTROLLED SYNTHESIS OF PENTALENIC ACID AND PENTALENENE [J].

HUDLICKY, T ;

SINAIZINGDE, G ;

NATCHUS, MG ;

RANU, BC ;

PAPADOPOLOUS, P .

TETRAHEDRON, 1987, 43 (23) :5685-5721

[6] TOTAL SYNTHESIS OF (+/-)-PENTALENENE, (+/-)-PENTALENIC ACID, AND (+/-)-DEOXYPENTALENIC ACID THROUGH AN INTRAMOLECULAR DOUBLE MICHAEL REACTION [J].

IHARA, M ;

KATOGI, M ;

FUKUMOTO, K ;

KAMETANI, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (11) :2963-2970

[7] SULFONE-BASED ELIMINATION-REACTIONS IN SYNTHESIS .2. DIUMYCINOL [J].

KOCIENSKI, P ;

TODD, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (08) :1783-1789

[8] SYNTHESIS OF (-)-ACORONE AND RELATED SPIROCYCLIC SESQUITERPENES [J].

MARX, JN ;

NORMAN, LR .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (11) :1602-1606

[9]

PROFITT JA, 1975, J ORG CHEM, V40, P27

[10] THE PAUSON-KHAND REACTION IN TRIQUINANE SYNTHESIS - APPROACHES TO PENTALENENE, PENTALENIC ACID, AND SILPHINENE [J].

ROWLEY, EG ;

SCHORE, NE .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (25) :6853-6861