The lithium amide induced rearrangement of epoxysulfones derived from bicyclo[2.2.1]heptane system

被引:9
作者
Arjona, O [1 ]
Menchaca, R [1 ]
Plumet, J [1 ]
机构
[1] Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
关键词
bicyclic aliphatic compounds; carbenes and carbenoids; epoxides; lithium amides;
D O I
10.1016/S0040-4020(00)00294-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Lithium amides induce rearrangement of the title compounds 1 to afford nortricyclanones 4 via a ketocarbene intermediate. Compounds 4 undergo hydride transfer reduction and imino aldol condensation to afford the other observed reaction products. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3901 / 3907
页数:7
相关论文
共 49 条
[1]   A convenient approach to the aminocyclitol fragment of pancratistatin from 7-oxanorbornenes [J].
Acena, JL ;
Arjona, O ;
Iradier, F ;
Plumet, J .
TETRAHEDRON LETTERS, 1996, 37 (01) :105-106
[2]   A STEREODIVERGENT ACCESS TO NATURALLY-OCCURRING AMINOCARBASUGARS FROM (PHENYLSULFONYL)-7-OXABICYCLO[2.2.1]HEPTANE DERIVATIVES - TOTAL SYNTHESIS OF PENTA-N,O-ACETYL-(+/-)-VALIDAMINE AND ITS C-1 AND C-2 STEREOISOMERS [J].
ACENA, JL ;
ARJONA, O ;
DELAPRADILLA, RF ;
PLUMET, J ;
VISO, A .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6419-6424
[3]   Total syntheses of (+/-)-cyclophellitol and (1R*,6S*)-cyclophellitol [J].
Acena, JL ;
Arjona, O ;
Plumet, J .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (10) :3360-3364
[4]  
ACENA JL, 1996, UNPUB THESIS U COMPL
[5]   A stereoselective synthesis of two epimeric polypropionate fragments with four adjacent chiral centers from 7-oxanorbornene derivatives [J].
Arjona, O ;
Menchaca, R ;
Plumet, J .
TETRAHEDRON LETTERS, 1998, 39 (37) :6753-6756
[6]  
BARTOK M, 1985, STEREOCHEMISTRY HETE, P1
[7]   CHEMICAL AND BIOLOGICAL SYNTHESIS OF CHIRAL EPOXIDES [J].
BESSE, P ;
VESCHAMBRE, H .
TETRAHEDRON, 1994, 50 (30) :8885-8927
[8]   Saturated oxygen heterocycles [J].
Burns, CJ ;
Middleton, DS .
CONTEMPORARY ORGANIC SYNTHESIS, 1996, 3 (03) :229-242
[9]  
BURNS CJ, 1994, SATURATED OXYGEN HET, V1, P23
[10]  
BURNS CJ, 1995, SATURATED OXYGEN HET, V2, P189