A bicyclo[3.2.0]hept-3-en-6-one approach to prostaglandin intermediates

被引:20
作者
Marotta, E [1 ]
Righi, P [1 ]
Rosini, G [1 ]
机构
[1] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy
关键词
D O I
10.1021/ol006664v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The substituted cyclopentanic structures, 6-benzyloxymethyl-7-hydroxy-2-oxabicyclo (1), a Corey lactone derivative, and 6-exo-benzyloxymethyl-2-oxabicyclo[3.3.0]oct-7-en-3-one (2), have been obtained stereoselectively through the bicyclo[3.2.0]hept-3-en-6-one approach via 5-benzyloxymethyl-3-hydroxy-6-heptenoic acid, easily accessible from the inexpensive monoprotected cis-2-butene-1,4-diol.
引用
收藏
页码:4145 / 4148
页数:4
相关论文
共 75 条
[51]  
Rathke M.W., 1975, Org. React, V22, P423, DOI [10.1002/0471264180.or022.04, DOI 10.1002/0471264180.OR022.04]
[52]   REFORMATSKY REACTION AT ROOM TEMPERATURE AND IN PRESENCE OF TRIMETHYL BORATE - IMPROVED PROCEDURES FOR PREPARATION OF BETA-HYDROXY ESTERS [J].
RATHKE, MW ;
LINDERT, A .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (11) :3966-&
[53]  
Reformatsky S., 1887, Chem. Ber, V20, P1210, DOI DOI 10.1002/CBER.188702001268
[54]  
Roberts S. M., 1982, NEW SYNTHETIC ROUTES
[55]  
Roland A, 1996, B SOC CHIM FR, V133, P1149
[56]   Total synthesis of the marine sesquiterpenoid raikovenal through a novel utilization of the bicyclo[3.2.0]heptenone approach [J].
Rosini, G ;
Laffi, F ;
Marotta, E ;
Pagani, I ;
Righi, P .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07) :2389-2391
[57]  
ROSINI G, 1995, Patent No. 0521571
[58]  
ROSINI G, 1995, Patent No. 9220019575
[59]  
ROSINI G, 1997, ORG SYNTH, V74, P158
[60]   A STEREOCHEMICALLY GENERAL-SYNTHESIS OF 2-DEOXYHEXOSES VIA THE ASYMMETRIC ALLYLBORATION OF 2,3-EPOXYALDEHYDES [J].
ROUSH, WR ;
STRAUB, JA ;
VANNIEUWENHZE, MS .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1636-1648