VINYL CARBANIONS .46. A CONVENIENT STEREOSELECTIVE SYNTHESIS OF A (-)-VERTINOLIDE PRECURSOR

被引：14

作者：

DATTA, A ^{[1
]}

DATTA, D ^{[1
]}

SCHMIDT, RR ^{[1
]}

机构：

[1] UNIV CONSTANCE,FACHBEREICH CHEM,POSTFACH 5560,W-7750 CONSTANCE,GERMANY

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 52期

关键词：

D O I：

10.1016/S0040-4039(00)74710-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short practical method for die enantioselective synthesis of (-)-vertinolide precursor 2 is described. The readily available chiral beta-alkoxy substituted acrylate 7 has been reacted with ethyl levulinate to form the tetronic acid nucleus 8, which in three subsequent steps was converted to the known precursor 2 in high overall yield.

引用

页码：8035 / 8038

页数：4

共 13 条

[1] DIRECTED METALLATIONS OF 4-ETHYLIDENETETRONIC ACID AND ITS DERIVATIVES AS A SYNTHETIC ENTRY TO NATURAL 4-OXY-2-FURANONES [J].

CLEMO, NG ;

PATTENDEN, G .

TETRAHEDRON LETTERS, 1982, 23 (05) :581-584

[2]

DATTA A, 1992, SYNLETT, P429

[3] NEW APPROACH TO CHIRAL 5,5-DISUBSTITUTED TETRONIC ACIDS - ENANTIOSELECTIVE SYNTHESIS OF (-)-VERTINOLIDE [J].

DESMAELE, D .

TETRAHEDRON, 1992, 48 (14) :2925-2934

[4]

HAYNES LJ, 1960, Q REV, V14, P2292

[5]

HIRSENKORN R, 1990, LIEBIGS ANN CHEM, P883

[6]

JATZKE H, 1990, SYNLETT, P191

[7]

MIYATA O, 1982, TETRAHEDRON LETT, V23, P1793, DOI 10.1016/S0040-4039(00)86743-X

[8]

SCHMIDT RR, 1983, B SOC CHIM BELG, V92, P825

[9] SYNTHESIS OF (S)-(-)-VERTINOLIDE [J].

TAKAIWA, A ;

YAMASHITA, K .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1984, 48 (04) :961-963

[10]

TAKAIWA A, 1983, AGR BIOL CHEM TOKYO, P429

← 1 2 →