THE REARRANGEMENT OF SOME CYCLOPENTANONE-ARYLOXIMES - SYNTHESIS OF (+/-)-APLYSIN, (+/-)-FILIFORMIN AND OF THEIR DEBROMO ANALOGS

被引:23
作者
LARONZE, JY
ELBOUKILI, R
PATIGNY, D
DRIDI, S
CARTIER, D
LEVY, J
机构
[1] Laboratoire de Transformations et Synthèse de Substances Naturelles, associé au CNRS, Université de Reims-Champagne-Ardenne, 51096 Reims Cédex, 51, rue Cognacq-Jay
关键词
SESQUITERPENE; APLYSIN; FILIFORMIN; REARRANGEMENT OF ARYLOXIMES; CYCLOPENTANODIHYDROBENZOFURANES; DIASTEREOSELECTIVE EQUILIBRATION-ALKYLATION OF A LACTOL;
D O I
10.1016/S0040-4020(01)96049-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
upon acid catalyzed rearrangement after Sheradsky, the aryloximes A gave the tricyclic aminals C, which suffered hydrolysis to lactols E. The unique alcohol 29 was then prepared through a highly stereoselective equilibration-reductive alkylation of the epimeric mixture of lactols 22a,b. Two routes, one of which was stereospecific, allowed cyclization of 29 to (+/-)-aplysin 34. The yield was 2.5 % from oximes 2a,b. The isomeric epi-aplysin 35 and filiformin 36 were also obtained from 29. The debromo analogues 37, 38 and 39 and their trideutero derivatives 41, 42 and 43 were synthesized along similar line and allowed unequivocal structure elucidation by NMR spectroscopy.
引用
收藏
页码:10003 / 10014
页数:12
相关论文
共 22 条
[1]  
ALEMAGNA A, 1987, SYNTHESIS-STUTTGART, P192
[2]   STEREOCONTROLLED SYNTHESIS OF (+/-)-DEBROMOAPLYSIN, (+/-)-APLYSIN, (+/-)-DEBROMOAPLYSINOL, (+/-)-APLYSINOL, AND (+/-)-ISOAPLYSIN [J].
BISWAS, S ;
GHOSH, A ;
VENKATESWARAN, RV .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3498-3502
[3]   SYNTHESIS OF PHENOXYAMINES [J].
CASTELLINO, AJ ;
RAPOPORT, H .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (08) :1348-1352
[4]   DYNAMIC STEREOCHEMISTRY OF ALDOLIZATION .20. STUDY OF STEREOCHEMICAL COMPOSITION VERSUS TIME - QUANTITATIVE DETERMINATION OF KINETIC AND THERMODYNAMIC STEREOSELECTIVITIES [J].
DUBOIS, JE ;
FORT, JF .
TETRAHEDRON, 1972, 28 (06) :1653-&
[5]   PREPARATION AND REARRANGEMENT OF TRICHOTHECANE-LIKE COMPOUNDS - SYNTHESIS OF APLYSIN AND FILIFORMIN [J].
GOLDSMITH, DJ ;
JOHN, TK ;
KWONG, CD ;
PAINTER, GR .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (20) :3989-3993
[6]  
HORNING EC, 1955, ORGANIC SYNTHESES CO, V3, P130
[7]   LAURINTEROL, DEBROMOLAURINTEROL AND ISOLAURINTEROL,CONSTITUENTS OF LAURENCIA-INTERMEDIA YAMADA [J].
IRIE, T ;
SUZUKI, M ;
KUROSAWA, E ;
MASAMUNE, T .
TETRAHEDRON, 1970, 26 (13) :3271-&
[8]   NEW LAURENE DERIVATIVES FROM LAURENCIA-FILIFORMIS [J].
KAZLAUSKAS, R ;
MURPHY, PT ;
QUINN, RJ ;
WELLS, RJ .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (11) :2533-2539
[9]   THE SHERADSKY REARRANGEMENT OF ALPHA,ALPHA'-DISUBSTITUTED CYCLOPENTANONE ARYLOXIMES - A SYNTHESIS OF THE SESQUITERPENES (+/-)-APLYSIN AND (+/-)-FILIFORMIN [J].
LARONZE, JY ;
ELBOUKILI, R ;
CARTIER, D ;
LARONZE, J ;
LEVY, J .
TETRAHEDRON LETTERS, 1989, 30 (17) :2229-2232
[10]   METHYLENE-INDOLINES, INDOLENINES AND INDOLENINIUMS .22. THE FISCHER INDOLIZATION OF SOME SUBSTITUTED CYCLOPENTANONES [J].
LARONZE, JY ;
ELBOUKILI, R ;
ROYER, D ;
LEVY, J .
TETRAHEDRON, 1991, 47 (27) :4915-4926