Investigation of the synthesis of angular tricyclic compounds by intramolecular Pauson-Khand reaction of exo- and endo-cyclic enynes

被引：36

作者：

Ishizaki, M ^{[1
]}

Iwahara, K ^{[1
]}

Niimi, Y ^{[1
]}

Satoh, H ^{[1
]}

Hoshino, O ^{[1
]}

机构：

[1] Tokyo Univ Sci, Fac Pharmaceut Sci, Shinjuku Ku, Tokyo 1620826, Japan

来源：

TETRAHEDRON | 2001年 / 57卷 / 14期

关键词：

Pauson-Khand reaction; exocyclic enyne; endocyclic enyne; angular tricyclic compound;

D O I：

10.1016/S0040-4020(01)00151-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular Pauson-Khand reaction of various alkynyl exo-alkylidene-cyclohexanes and -pentane gives angular type 6-5-5 and 5-5-5 tricyclic compounds in good to high yield. The present reaction also offers convenient construction of two contiguous quaternary centers, which could not be synthesized from alkynyl endo-cycloolefins. Scope and limitation of the present reaction of various exo- and endo-cyclic enynes are also described. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2729 / 2738

页数：10

共 63 条

[1] SYNTHESIS AND CHIROPTICAL PROPERTIES OF C3-PERHYDROTRIQUINACENE DERIVATIVES [J].

ALMANSA, C ;

MOYANO, A ;

SERRATOSA, F .

TETRAHEDRON, 1988, 44 (09) :2657-2662

[2] INTRAMOLECULAR FREE-RADICAL CYCLIZATIONS ONTO ENOL ETHERS - A GENERAL-SYNTHESIS OF ALPHA-ALKYL-BETA-OXY-GAMMA-BUTYROLACTONES AND ALPHA-METHYLENE-BETA-OXY-GAMMA-BUTYROLACTONES [J].

BEGLEY, MJ ;

LADLOW, M ;

PATTENDEN, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (05) :1095-1106

[3] ASYMMETRIC PAUSON-KHAND CYCLIZATION - A FORMAL TOTAL SYNTHESIS OF NATURAL BREFELDIN-A [J].

BERNARDES, V ;

KANN, N ;

RIERA, A ;

MOYANO, A ;

PERICAS, MA ;

GREENE, AE .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6670-6671

[4] THE KHAND REACTION OF SOME TRISUBSTITUTED ALKENES - USES OF THE CATALYTIC VERSION OF THE REACTION [J].

BILLINGTON, DC ;

KERR, WJ ;

PAUSON, PL ;

FARNOCCHI, CF .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 356 (02) :213-219

[5] Versatile synthesis of enantiomerically pure 2-alkoxy-1-ethynylcyclopropanes and their application in the synthesis of enantiomerically pure bicyclo-[3.3.0]oct-1-en-3-ones [J].

Brase, S ;

Schomenauer, S ;

McGaffin, G ;

Stolle, A ;

deMeijere, A .

CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (05) :545-555

[6] Recent advances in the Pauson-Khand reaction and related [2+2+1] cycloadditions [J].

Brummond, KM ;

Kent, JL .

TETRAHEDRON, 2000, 56 (21) :3263-3283

[7] A short synthesis of the potent antitumor agent (±)-hydroxymethylacylfulvene using an allenic Pauson-Khand type cycloaddition [J].

Brummond, KM ;

Lu, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (21) :5087-5088

[8] A short synthesis of (-)-dendrobine [J].

Cassayre, J ;

Zard, SZ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (25) :6072-6073

[9] ASYMMETRIC APPROACH TO PAUSON-KHAND BICYCLIZATION - ENANTIOSELECTIVE FORMAL SYNTHESIS OF HIRSUTENE [J].

CASTRO, J ;

SORENSEN, H ;

RIERA, A ;

MORIN, C ;

MOYANO, A ;

PERICAS, MA ;

GREENE, AE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (25) :9388-9389

[10] Ready access to bicyclo[5.3.0]decan-1-ones and to bicyclo[6.3.0]undecan-1-ones by intramolecular Pauson-Khand reactions using a temporary sulfur bridge [J].

Castro, J ;

Moyano, A ;

Pericas, MA ;

Riera, A .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3346-3351

← 1 2 3 4 5 6 7 →