CYCLIZATION OF POLYENES .49. CYCLIZATION OF EPOXYNEOCEMBRENE DERIVATIVES TO SECOTRINERVITANES

被引：11

作者：

HIRUKAWA, T ^{[1
]}

KOARAI, A ^{[1
]}

KATO, T ^{[1
]}

机构：

[1] SCI UNIV TOKYO,FAC SCI,DEPT CHEM,1-3 KAGURAZAKA,SHINJYUKU KU,TOKYO 162,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 14期

关键词：

D O I：

10.1021/jo00014a036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Four stereoisomers of epoxyneocembrene derivatives 5-8 were treated with BF3.OEt2 as potential model reactions for the proposed biogenesis of secotrinervitane-type diterpenoids (Scheme I). Two of them (5 and 6) afforded secotrinervitane derivatives, while the remaining isomers 7 and 8 gave no cyclization products (Table I). The natural product, secotrinervitene-2-beta,3-alpha-diol (2a) was synthesized from 5 in dl-form.

引用

页码：4520 / 4525

页数：6

共 10 条

[1] NEOCEMBRENE-A, A TERMITE TRAIL PHEROMONE [J].

BIRCH, AJ ;

BROWN, WV ;

CORRIE, JET ;

MOORE, BP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (21) :2653-&

[2] SECOTRINERVITANE, A NOVEL BICYCLIC DITERPENE SKELETON FROM A TERMITE SOLDIER [J].

BRAEKMAN, JC ;

DALOZE, D ;

DUPONT, A ;

PASTEELS, J ;

TURSCH, B ;

DECLERCQ, JP ;

GERMAIN, G ;

VANMEERSSCHE, M .

TETRAHEDRON LETTERS, 1980, 21 (28) :2761-2762

[3] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].

COREY, EJ ;

VENKATESWARLU, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+

[4] CYCLIZATION OF POLYENES .47. THE 1ST SYNTHESIS OF (+/-)-3-ALPHA-ACETOXY-15-BETA-HYDROXY-7,16-SECOTRINERVITA-7,11-DIENE, DEFENSE SUBSTANCE FROM A TERMITE SOLDIER [J].

KATO, T ;

HIRUKAWA, T ;

UYEHARA, T ;

YAMAMOTO, Y .

TETRAHEDRON LETTERS, 1987, 28 (13) :1439-1442

[5] CYCLIZATION OF POLYENES .46. SYNTHESIS OF (+/-)-ASPERDIOL, AN ANTICANCER CEMBRENOID [J].

KATO, T ;

AOKI, M ;

UYEHARA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (09) :1803-1810

[6] A BIOGENETIC SYNTHESIS OF (+/-)-SECOTRINERVITEN-2-BETA,3-ALPHA-DIOL [J].

KATO, T ;

HIRUKAWA, T ;

YAMAMOTO, Y .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (13) :977-978

[7] CYCLIZATION OF POLYENES .25. CONFORMATIONAL STUDY OF CEMBRENE TYPE DITERPENES BY X-RAY ANALYSIS [J].

KATO, T ;

KABUTO, C ;

KIM, KH ;

TAKAYANAGI, H ;

UYEHARA, T ;

KITAHARA, Y .

CHEMISTRY LETTERS, 1977, (07) :827-830

[8] CYCLIZATION OF POLYENES .17. SYNTHESIS AND PHEROMONE ACTIVITY OF D,L-NEOCEMBRENE [J].

KITAHARA, Y ;

KATO, T ;

KOBAYASHI, T ;

MOORE, BP .

CHEMISTRY LETTERS, 1976, (03) :219-222

[9]

PARIL VD, 1973, TETRAHEDRON, V29, P341

[10] LONGIPENOL, A NOVEL TETRACYCLIC DITERPENE FROM THE TERMITE SOLDIER LONGIPEDITERMES-LONGIPES [J].

PRESTWICH, GD ;

TEMPESTA, MS ;

TURNER, C .

TETRAHEDRON LETTERS, 1984, 25 (15) :1531-1532

← 1 →