SYNTHESIS OF [5.5.5.5]FENESTRANES BY PD-CATALYZED CARBONYLATION-CYCLIZATION

被引：41

作者：

KEESE, R

GUIDETTIGREPT, R

HERZOG, B

机构：

[1] Institut für organische Chemie, Universität Bern, CH - 3012 Bern

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 09期

关键词：

D O I：

10.1016/S0040-4039(00)91897-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pd-catalyzed reaction of 3-acetoxy-8-butenyl- (9) and 8-but-3-inyl-bicyclo[3.3.0]oct-1-ene (11) with CO in CH3COOH lead via double annulation to all-cis[5.5.5.5]fenestranes.

引用

页码：1207 / 1210

页数：4

共 12 条

[1] METAL-PROMOTED CYCLIZATION .19. NOVEL BICYCLIZATION OF ENYNES AND DIYNES PROMOTED BY ZIRCONOCENE DERIVATIVES AND CONVERSION OF ZIRCONABICYCLES INTO BICYCLIC ENONES VIA CARBONYLATION [J].

NEGISHI, E ;

HOLMES, SJ ;

TOUR, JM ;

MILLER, JA ;

CEDERBAUM, FE ;

SWANSON, DR ;

TAKAHASHI, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3336-3346

[2] REGIOCONTROLLED AND STEREOCONTROLLED CATALYTIC PALLADIUM-ENE-TYPE AND NICKEL-ENE-TYPE CYCLIZATIONS [J].

OPPOLZER, W .

PURE AND APPLIED CHEMISTRY, 1990, 62 (10) :1941-1948

[3] DIASTEREOCONTROLLED NICKEL(0) CATALYZED AND PALLADIUM(0) CATALYZED METALLO-ENE-TYPE CYCLIZATIONS CARBONYLATIONS [J].

OPPOLZER, W ;

KELLER, TH ;

BEDOYAZURITA, M ;

STONE, C .

TETRAHEDRON LETTERS, 1989, 30 (43) :5883-5886

[4] PREPARATION OF A KEY INTERMEDIATE FOR THE SYNTHESIS OF THE (+/-)-PENTALENOLACTONE-E METHYL-ESTER BY CATALYTIC PALLADIUM-ENE CYCLIZATION/METHOXYCARBONYLATION [J].

OPPOLZER, W ;

XU, JZ ;

STONE, C .

HELVETICA CHIMICA ACTA, 1991, 74 (03) :465-468

[5] INTRAMOLECULAR, STOICHIOMETRIC (LI, MG, ZN) AND CATALYTIC (NI, PD, PT) METALLO-ENE REACTIONS IN ORGANIC-SYNTHESIS [J].

OPPOLZER, W .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (01) :38-52

[6]

Oppolzer W, 1989, ANGEW CHEM, V101, P39

[7] THE KHAND REACTION - A CONVENIENT AND GENERAL-ROUTE TO A WIDE-RANGE OF CYCLOPENTENONE DERIVATIVES [J].

PAUSON, PL .

TETRAHEDRON, 1985, 41 (24) :5855-5860

[8] PLANARIZATION OF TETRACOORDINATE CARBON-ATOM - SYNTHESIS OF THE BRIGDED ALL-CIS-[5.5.5.5]FENESTRANE 13-OXAPENTACYCLO[5.5.2.1(1,7).0(4,15).0(10,15)]PENTADECAN-14-ONE [J].

PFENNINGER, A ;

ROESLE, A ;

KEESE, R .

HELVETICA CHIMICA ACTA, 1985, 68 (02) :493-507

[9] TRANSITION-METAL-MEDIATED CYCLO-ADDITION REACTIONS OF ALKYNES IN ORGANIC-SYNTHESIS [J].

SCHORE, NE .

CHEMICAL REVIEWS, 1988, 88 (07) :1081-1119

[10] N-OXIDE PROMOTED PAUSON-KHAND CYCLIZATIONS AT ROOM-TEMPERATURE [J].

SHAMBAYATI, S ;

CROWE, WE ;

SCHREIBER, SL .

TETRAHEDRON LETTERS, 1990, 31 (37) :5289-5292

← 1 2 →