First total synthesis and structural elucidation of (-)-goniofupyrone

被引:22
作者
Mukai, C
Hirai, S
Kim, IJ
Hanaoka, M
机构
[1] Faculty of Pharmaceutical Sciences, Kanazawa University, Kanazawa 920, Takara-machi
关键词
D O I
10.1016/0040-4039(96)01085-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of (-)-goniofupyrone isolated from Goniothalamus giganteus, was accomplished in a stereoselective manner from (+)-tricarbonyl(eta(6)-2-trimethylsilylbenzaldehyde)-chromium(0) complex. This synthesis unambiguously established the relative and absolute stereochemistry of (-)-goniofupyrone. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:5389 / 5392
页数:4
相关论文
共 16 条
[1]   A STEREOSELECTIVE APPROACH TO ANNULATED TETRAHYDROFURANS BY IODOCYCLISATIONS OF 2-ALKENYLCYCLOALKAN-1-OLS [J].
BARKS, JM ;
KNIGHT, DW ;
WEINGARTEN, GG .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (06) :719-720
[2]   GONIOTHALENOL - A NOVEL, BIOACTIVE, TETRAHYDROFURANO-2-PYRONE FROM GONIOTHALAMUS-GIGANTEUS (ANNONACEAE) [J].
ELZAYAT, AAE ;
FERRIGNI, NR ;
MCCLOUD, TG ;
MCKENZIE, AT ;
BYRN, SR ;
CASSADY, JM ;
CHANG, CJ ;
MCLAUGHLIN, JL .
TETRAHEDRON LETTERS, 1985, 26 (08) :955-956
[3]   3 NEW BIOACTIVE STYRYLLACTONES FROM GONIOTHALAMUS-GIGANTEUS (ANNONACEAE) [J].
FANG, XP ;
ANDERSON, JE ;
CHANG, CJ ;
MCLAUGHLIN, JL .
TETRAHEDRON, 1991, 47 (47) :9751-9758
[4]   ENANTIODIVERGENT SYNTHESIS OF (+) AND (-) ALTHOLACTONE FROM D-GLUCOSE - PREPARATION AND CYTO-TOXIC ACTIVITY OF ANALOGS [J].
GESSON, JP ;
JACQUESY, JC ;
MONDON, M .
TETRAHEDRON, 1989, 45 (09) :2627-2640
[5]  
GRIECO PA, 1978, TETRAHEDRON LETT, P419
[6]   A VERSATILE PROTOCOL FOR THE STEREOCONTROLLED ELABORATION OF VICINAL SECONDARY AND TERTIARY CENTERS OF RELEVANCE TO NATURAL PRODUCT SYNTHESIS [J].
HANESSIAN, S ;
MURRAY, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (06) :1170-1172
[7]   AN ACYLNITROSO CYCLOADDITION APPROACH TO THE SYNTHESIS OF HIGHLY OXYGENATED INDOLIZIDINE ALKALOIDS [J].
KECK, GE ;
ROMER, DR .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) :6083-6089
[8]  
LEY SV, 1994, SYNTHESIS-STUTTGART, P639
[9]   THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].
MITSUNOBU, O .
SYNTHESIS-STUTTGART, 1981, (01) :1-28
[10]   AN OPTICALLY-ACTIVE CHROMIUM(0)-COMPLEXED BENZALDEHYDE DERIVATIVE IN ORGANIC-SYNTHESIS - A HIGHLY STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-GONIOFUFURONE [J].
MUKAI, C ;
KIM, IJ ;
HANAOKA, M .
TETRAHEDRON LETTERS, 1993, 34 (38) :6081-6082