Synthesis of bicyclo[4.n.1]alkanones

被引：10

作者：

Montalt, J ^{[1
]}

Linker, F ^{[1
]}

Ratel, F ^{[1
]}

Miesch, M ^{[1
]}

机构：

[1] Univ Strasbourg, Lab Chim Organ Synthet, CNRS, UMR 7123,Fac Chim, F-67008 Strasbourg, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 20期

关键词：

D O I：

10.1021/jo048923q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclic P-keto ester monoanions react with 1,4-dihalobutenes to give C-alkylated products which subsequently undergo a stereoselective S(N)2' O-alkylation reaction to yield functionalized enol ethers. When the starting material was ethyl cyclopentanone carboxylate, the C-alkylated product, treated with a base, directly afforded the functionalized bicyclo[4.2.1]nonanone. The enol ethers were submitted to a flash vacuum thermolysis (FVT) reaction to readily afford functionalized bicyclo[4.n.1] alkanones (n = 3, 4). This reaction sequence was applied to the synthesis of a functionalized tricyclo[7.4.1.0(1,5)]tetradecanone, which represents an analogue to the tricyclic core of ingenol.

引用

页码：6715 / 6721

页数：7

共 35 条

[1]

BARCO S, 1973, SYNTHESIS-STUTTGART, P216

[2] Isoxazole→benzisoxazole rearrangement promoted cascade reactions affording stereodefined polycycles [J].

Bode, JW ;

Uesuka, H ;

Suzuki, K .

ORGANIC LETTERS, 2003, 5 (04) :395-398

[3]

Cole BM, 1996, J ORG CHEM, V61, P7832

[4]

Dabrah TT, 1997, J ANTIBIOT, V50, P1

[5] CP-225,917 and CP-263,114: Novel ras farnesylation inhibitors from an unidentified fungus .2. Structure elucidation [J].

Dabrah, TT ;

Kaneko, T ;

Massefski, W ;

Whipple, EB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (07) :1594-1598

[6] MEDITERRANEOL A, A NOVEL REARRANGED DITERPENOID-HYDROQUINONE FROM THE MARINE ALGA CYSTOSEIRA-MEDITERRANEA [J].

FRANCISCO, C ;

BANAIGS, B ;

VALLS, R ;

CODOMIER, L .

TETRAHEDRON LETTERS, 1985, 26 (22) :2629-2632

[7] MEDITERRANEOLS - A NOVEL BIOLOGICALLY-ACTIVE CLASS OF REARRANGED DITERPENOID METABOLITES FROM CYSTOSEIRA-MEDITERRANEA (PHEOPHYTA) [J].

FRANCISCO, C ;

BANAIGS, B ;

TESTE, J ;

CAVE, A .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (07) :1115-1120

[8]

HECKER E, 1968, CANCER RES, V28, P2338

[9] MANGANESE(III)-BASED OXIDATIVE FREE-RADICAL CYCLIZATION OF UNSATURATED BETA-KETO-ESTERS, 1,3-DIKETONES, AND MALONATE DIESTERS [J].

KATES, SA ;

DOMBROSKI, MA ;

SNIDER, BB .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (08) :2427-2436

[10] Synthetic studies of ingenol:: synthesis of in,out-tricyclo[7.4.1.01,5]tetradecan-14-one [J].

Kigoshi, H ;

Suzuki, Y ;

Aoki, K ;

Uemura, D .

TETRAHEDRON LETTERS, 2000, 41 (20) :3927-3930

← 1 2 3 4 →