Diquinane synthesis based on anionic [1,3] sigmatropic rearrangements of an oxy-cope system incorporated in the bicyclo[3.2.1]oct-6-ene framework

被引：7

作者：

Seki, K

Kiyokawa, W

Hashimoto, H

Uyehara, T

Ueno, M

Sato, T

机构：

[1] UTSUNOMIYA UNIV, FAC ENGN, DEPT APPL CHEM, UTSUNOMIYA, TOCHIGI 321, JAPAN

[2] TOHOKU UNIV, FAC SCI, INSTRUMENTAL ANALYT CTR CHEM, SENDAI, MIYAGI 98077, JAPAN

来源：

CHEMISTRY LETTERS | 1996年 / 12期

关键词：

D O I：

10.1246/cl.1996.1035

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of 2-vinylbicyclo[3.2.1]oct-6-en-2-ols with KH in toluene gave mainly [5-5] fused-ring compounds through a [1,3] sigmatropic shift.

引用

页码：1035 / 1036

页数：2

共 14 条

[1] A SHORT SYNTHESIS OF THE TRICYCLIC RING-SYSTEM OF VINIGROL [J].

DEVAUX, JF ;

HANNA, I ;

LALLEMAND, JY .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) :2349-2350

[2] DIASTEREOSELECTIVITIES ASSOCIATED WITH THE 1,2-ADDITION OF CHIRAL (RACEMIC) CYCLOPENTENYL ORGANOMETALLICS TO BICYCLO[2.2.2]OCTENONES [J].

DOYON, J ;

HE, W ;

PAQUETTE, LA .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (08) :2033-2042

[3] ULTRASOUND ASSISTED PREPARATION OF ORGANOCERIUM REAGENTS [J].

GREEVES, N ;

LYFORD, L .

TETRAHEDRON LETTERS, 1992, 33 (33) :4759-4760

[4] TANDEM COPE-COPE REARRANGEMENTS [J].

GUEVEL, R ;

PAQUETTE, LA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) :1776-1784

[5] REACTIONS OF CARBONYL-COMPOUNDS WITH GRIGNARD-REAGENTS IN THE PRESENCE OF CERIUM CHLORIDE [J].

IMAMOTO, T ;

TAKIYAMA, N ;

NAKAMURA, K ;

HATAJIMA, T ;

KAMIYA, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4392-4398

[6]

MORI K, 1995, SYNTHESIS-STUTTGART, P845, DOI 10.1055/s-1995-4004

[7]

PAQUETTE LA, 1990, SYNLETT, P67

[8] A MEANS FOR STEREOCONTROLLED INTRODUCTION OF THE C-2 OXYGEN SUBSTITUENT IN FUNCTIONALIZED CIS-TRICYCLO[9.3.1.03,8]PENTADECANONES RELATED TO TAXOL [J].

PAQUETTE, LA ;

HUBER, SK ;

THOMPSON, RC .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (24) :6874-6882

[9] STEREOCONTROLLED CONSTRUCTION OF COMPLEX CYCLIC-KETONES VIA OXY-COPE REARRANGEMENT [J].

PAQUETTE, LA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (06) :609-626

[10] SYNTHETIC EQUIVALENTS OF THE TAXOL C,D RING-SYSTEM - EXAMINATION OF NUCLEOPHILIC BICYCLIC OXETANES AND LESS-STRAINED ACETONIDE EQUIVALENTS [J].

PAQUETTE, LA ;

THOMPSON, RC .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (18) :4952-4962

← 1 2 →