FORMATION OF ORTHOESTERS IN THE SHARPLESS ASYMMETRIC EPOXIDATION - HEMISYNTHESIS OF LABDANES

被引:19
作者
URONES, JG
MARCOS, IS
BASABE, P
SEXMERO, MJ
DIEZ, D
GARRIDO, NM
PRIETO, JES
机构
[1] Departamento de Química Orgánica Universidad, Salamanca Facultad de Químicas, 37008 Salamanca
关键词
D O I
10.1016/S0040-4020(01)82030-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The orthoesters, 4a and 4b were obtained from treatment of methyl-7,13E-labdadien-17-oate, 3, under Sharpless asymmetric epoxidation conditions . The hydrolysis followed by dehydration of the orthoesters led to the synthesis of two new diterpenic acids isolated from Halimium viscosum : 14R,15-dihydroxy-7,13(16)-labdadien-17-oic and 14S,15.dihydroxy-7, 13(16)-labdadien-17-oic. © 1990.
引用
收藏
页码:2495 / 2502
页数:8
相关论文
共 15 条
[1]   RULES FOR RING-CLOSURE - RING FORMATION BY CONJUGATE ADDITION OF OXYGEN NUCLEOPHILES [J].
BALDWIN, JE ;
THOMAS, RC ;
KRUSE, LI ;
SILBERMAN, L .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (24) :3846-3852
[2]   TI(O-I-PR)4-MEDIATED NUCLEOPHILIC OPENINGS OF 2,3-EPOXY ALCOHOLS - A MILD PROCEDURE FOR REGIOSELECTIVE RING-OPENING [J].
CARON, M ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1557-1560
[3]   CHIRALLY DIRECTED SYNTHESIS OF (-)-METHYL "5(S),6(S),OXIDO-7-HYDROXYHEPTANOATE .1. KEY INTERMEDIATE FOR THE TOTAL SYNTHESIS OF LEUKOTRIENE-A, LEUKOTRIENE-C, LEUKOTRIENE-D, AND LEUKOTRIENE-E [J].
COREY, EJ ;
HASHIMOTO, SI ;
BARTON, AE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (03) :721-722
[4]   BASE-PROMOTED REACTIONS OF EPOXIDES .V. 1-ALKYLCYCLOALKENE OXIDES [J].
CRANDALL, JK ;
LIN, LHC .
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (06) :2375-&
[5]  
DEPASCUAL J, 1986, PHYTOCHEMISTRY, V25, P711
[6]   THE HYDROLYSIS OF CIS AND TRANS METHOXY BICYCLIC AND TRICYCLIC ORTHO-ESTERS - EVIDENCE FOR A CHAIR BOAT INVERSION PRIOR TO BREAKDOWN IN SOME HEMIORTHOESTER TETRAHEDRAL INTERMEDIATES [J].
DESLONGCHAMPS, P ;
GUAY, D ;
CHENEVERT, R .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1985, 63 (09) :2493-2500
[7]   THE PRODUCTS OF HYDROLYSIS OF CYCLIC ORTHO-ESTERS AS A FUNCTION OF PH AND THE THEORY OF STEREOELECTRONIC CONTROL [J].
DESLONGCHAMPS, P ;
LESSARD, J ;
NADEAU, Y .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1985, 63 (09) :2485-2492
[8]  
Deslongchamps P., 1983, STEREOELECTRONIC EFF
[9]   ABSOLUTE CONFIGURATIONAL STUDIES OF VICINAL GLYCOLS AND AMINO ALCOHOLS .2. WITH PR(DPM)3 [J].
DILLON, J ;
NAKANISHI, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (19) :5417-5422
[10]   ABSOLUTE STEREOCHEMISTRY OF THE TRIOL MOIETY OF GYMNOPRENOLS - A REINVESTIGATION [J].
HANSON, RM .
TETRAHEDRON LETTERS, 1984, 25 (35) :3783-3786