Synthesis of liverwort sesquiterpene (-)-isocuparene(herbertene) via a Diels-Alder reaction using phenylethylamine as chiral auxiliary

被引：24

作者：

Tori, M

Miyake, T

Hamaguchi, T

Sono, M

机构：

[1] Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima 770, Yamashiro cho

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 16期

关键词：

D O I：

10.1016/S0957-4166(97)00313-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The imine of 2-methylcyclopentanone with (S)(-)-phenylethylamine was subjected to reaction with methyl propiolate and the product was transformed into (-)-isocuparene by use of a Diels-Alder reaction to construct the aromatic ring. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：2731 / 2738

页数：8

相关论文

共 21 条

[1] Enantioselective synthesis of cuparane sesquiterpenes. Synthesis of (-)-cuparene and (-)-delta-cuparenol [J].

Abad, A ;

Agullo, C ;

Arno, M ;

Cunat, AC ;

Garcia, MT ;

Zaragoza, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17) :5916-5919

[2] CONFORMATIONAL CONTROL IN THE CYCLIZATION OF AN UNSATURATED VINYLLITHIUM - SYNTHESIS OF (+/-)-LAURENE [J].

BAILEY, WF ;

JIANG, XL ;

MCLEOD, CE .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (24) :7791-7795

[3] A FORMAL TOTAL SYNTHESIS OF (+/-)-HERBERTENE [J].

BANERJEE, AK ;

PENAMATHEUD, CA ;

DECARRASCO, MC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (08) :2485-2490

[4] An efficient synthesis of alpha-cuparenone [J].

Chavan, SP ;

Ravindranathan, T ;

Patil, SS ;

Dhondge, VD ;

Dantale, SW .

TETRAHEDRON LETTERS, 1996, 37 (15) :2629-2630

[5] Total synthesis of herbertenediol, an isocuparane sesquiterpene isolated from liverworts [J].

Fukuyama, Y ;

Kiriyama, Y ;

Kodama, M .

TETRAHEDRON LETTERS, 1996, 37 (08) :1261-1264

[6] NOVEL NEUROTROPHIC ISOCUPARANE-TYPE SESQUITERPENE DIMERS, MASTIGOPHORENES-A, MASTIGOPHORENE-B, MASTIGOPHORENE-C AND MASTIGOPHORENE-D, ISOLATED FROM THE LIVERWORT MASTIGOPHORA-DICLADOS [J].

FUKUYAMA, Y ;

ASAKAWA, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (11) :2737-2741

[7] A NOVEL ROUTE TO CYCLOPROPANES FROM OLEFINS [J].

FURUKAWA, J ;

KAWABATA, N ;

NISHIMURA, J .

TETRAHEDRON LETTERS, 1966, (28) :3353-+

[8] A SYNTHETIC APPROACH TO CUPARANE AND HERBERTANE SESQUITERPENOIDS FROM A COMMON INTERMEDIATE [J].

HO, TL ;

CHANG, MH .

TETRAHEDRON LETTERS, 1994, 35 (27) :4819-4822

[9]

ISHIBASHI H, 1990, CHEM PHARM BULL, V38, P1738

[10] INTERNAL ACTIVATION OF ACRYLATE-TYPE DIENOPHILES IN DIELS-ALDER REACTIONS [J].

KAN, T ;

OHFUNE, Y .

TETRAHEDRON LETTERS, 1995, 36 (06) :943-946