Stereoselective approach to the BCD framework of richardianidins via intramolecular Reformatsky-type reaction promoted by diethylaluminum chloride

被引:9
作者
Sanchez, M [1 ]
Bermejo, F [1 ]
机构
[1] UNIV SALAMANCA,FAC QUIM,DEPT QUIM ORGAN,E-37008 SALAMANCA,SPAIN
关键词
D O I
10.1016/S0040-4039(97)01104-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The tricyclic derrivative (10d) has been prepared by intramolecular Reformatsky addition of alpha-bromopropionate (8b) in the presence of diethylaluminum chloride and activated Zn. Transformation of (10d) into the tricyclic methyl ketone (12a) was accomplished by dehydration followed by oxidation under Wacker conditions with 75% overall yield. (C) 1997 Elsevier Science Ltd.
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收藏
页码:5057 / 5060
页数:4
相关论文
共 9 条
[1]   PREPARATION OF LACTONE SYSTEMS - TOTAL SYNTHESIS OF (+/-)-QUADRONE [J].
BORNACK, WK ;
BHAGWAT, SS ;
PONTON, J ;
HELQUIST, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (15) :4647-4648
[2]  
CASSADY JM, 1985, J ORG CHEM, V50, P916
[3]   METALATED CARBOXYLIC ACIDS .I. ALKYLATION [J].
CREGER, PL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (10) :2500-&
[4]  
HEATHCOCK CH, 1984, ASYMMETRIC SYNTHESIS, V3, pCH2
[5]  
MAHUNNAH R L A, 1985, Journal of Economic and Taxonomic Botany, V7, P505
[6]  
MARUOKA K, 1977, J AM CHEM SOC, V99, P7707
[7]   NOVEL 6,7-SECO-6,11-CYCLOLABDANE DITERPENES FROM CLUYTIA-RICHARDIANA [J].
MOSSA, JS ;
CASSADY, JM ;
KOZLOWSKI, JF ;
ZENNIE, TM ;
ANTOUN, MD ;
PELLECHIA, MG ;
MCKENZIE, AT ;
BYRN, SR .
TETRAHEDRON LETTERS, 1988, 29 (30) :3627-3630
[8]  
TSUJI J, 1976, TETRAHEDRON LETT, V34, P2975
[9]   ANTINEOPLASTIC AGENTS .38. CRYSTAL AND MOLECULAR-STRUCTURE OF UNUSUAL SPIRO DIHYDROFURAN DITERPENE NEPETAEFOLIN [J].
VONDREELE, RB ;
PETTIT, GR ;
ODE, RH ;
PERDUE, RE ;
WHITE, JD ;
MANCHAND, PS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (21) :6236-6240