A short and general approach to the synthesis of styryllactones:: (+)-goniodiol, its acetates and β-trifluoromethyl derivative, (+)-7-epi-goniodiol and (+)-9-deoxygoniopypyrone

被引：0

作者：

Chen, J ^{[1
]}

Lin, GQ ^{[1
]}

Wang, ZM ^{[1
]}

Liu, HQ ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

SYNLETT | 2002年 / 08期

关键词：

(+)-goniodiol; styryllactoncs; synthesis; asymmetric dihydroxylation; cross-coupling;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+)-Goniodiol, its acetates and beta-trifluoromethyl derivative, (+)-7-epi-Goniodiol and (+)-9-deoxygoniopypyrone, the representatives of styryllactones have been synthesized in a short and,general way. The key steps involve the regioselective asymmetric dihydroxylation and the palladium-catalyzed cross-coupling of cyclic allylic carbonate with vinyltributylstannane.

引用

页码：1265 / 1268

页数：4

共 29 条

[1]

Banks R. E., 1994, ORGANOFLUORINE CHEM

[2] NEW LIGANDS AND IMPROVED ENANTIOSELECTIVITIES FOR THE ASYMMETRIC DIHYDROXYLATION OF OLEFINS [J].

BECKER, H ;

KING, SB ;

TANIGUCHI, M ;

VANHESSCHE, KPM ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) :3940-3941

[3]

COLB HC, 1994, CHEM REV, V94, P2483

[4] IMPROVED ENANTIOSELECTIVITY IN ASYMMETRIC DIHYDROXYLATIONS OF TERMINAL OLEFINS USING PYRIMIDINE LIGANDS [J].

CRISPINO, GA ;

JEONG, KS ;

KOLB, HC ;

WANG, ZM ;

XU, DQ ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3785-3786

[5] 2 NEW STYRYL LACTONES, 9-DEOXYGONIOPYPYRONE AND 7-EPI-GONIOFUFURONE, FROM GONIOTHALAMUS-GIGANTEUS [J].

FANG, XP ;

ANDERSON, JE ;

CHANG, CJ ;

MCLAUGHLIN, JL ;

FANWICK, PE .

JOURNAL OF NATURAL PRODUCTS, 1991, 54 (04) :1034-1043

[6] GONIOHEPTOLIDE-A AND GONIOHEPTOLIDE-B - NOVEL 8-MEMBERED-RING LACTONES FROM GONIOTHALAMUS-GIGANTEUS (ANNONACEAE) [J].

FANG, XP ;

ANDERSON, JE ;

QIU, XX ;

KOZLOWSKI, JF ;

CHANG, CJ ;

MCLAUGHLIN, JL .

TETRAHEDRON, 1993, 49 (08) :1563-1570

[7] TOTAL SYNTHESIS OF (+)-ALTHOLACTONE (GONIOTHALENOL) FROM D-GLUCOSE [J].

GESSON, JP ;

JACQUESY, JC ;

MONDON, M .

TETRAHEDRON LETTERS, 1987, 28 (34) :3949-3952

[8] ENANTIOSPECIFIC SYNTHESES OF (+)-ALTHOLACTONE AND (-)-ALTHOLACTONE (GONIOTHALENOL) [J].

GILLHOULEY, JG ;

SHING, TKM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (14) :976-977

[9]

GRUMMITT O, 1963, ORG SYNTH COLL, V4, P771

[10]

HAMPER BC, 1991, ORG SYNTH, V70, P246

← 1 2 3 →