Natural cyclic α,β-enone monoterpenoids in nucleophilic addition reactions

被引:4
作者
Ishmuratov, G. Yu.
Kharisov, R. Ya.
Latypova, E. R.
Talipov, R. F.
机构
[1] Russian Acad Sci, Inst Organ Chem, Ufa Sci Ctr, Ufa 450054, Russia
[2] Bashkir State Univ, Ufa 450074, Russia
关键词
organometallic reagents; natural cyclic alpha; beta-enone monoterpenoids; Michael reaction; 1,2-and 1,4-addition reactions;
D O I
10.1007/s10600-006-0161-z
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The literature on transformations of natural cyclic alpha,beta-enone monoterpenoids into compounds of more complicated structure via 1,2- and 1,4-addition reactions was reviewed. The data were systematized according to the effects of the conditions and nature of the starting substrates on the selectivity of the 1,2- and 1,4-addition reactions.
引用
收藏
页码:367 / 388
页数:22
相关论文
共 82 条
[41]  
MARINO JP, 1975, TETRAHEDRON LETT, V45, P3901
[43]   Total synthesis of dihydroclerodin from (R)-(-)-carvone [J].
Meulemans, TM ;
Stork, GA ;
Macaev, FZ ;
Jansen, BJM ;
de Groot, A .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (25) :9178-9188
[44]   Enantioselective synthesis of highly functionalised cyclohexanones starting from R-(-)-carvone [J].
Meulemans, TM ;
Stork, GA ;
Jansen, BJM ;
de Groot, A .
TETRAHEDRON LETTERS, 1998, 39 (36) :6565-6568
[45]   TOTAL SYNTHESIS OF GLYCINOECLEPIN-A [J].
MURAI, A ;
TANIMOTO, N ;
SAKAMOTO, N ;
MASAMUNE, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (06) :1985-1986
[46]   Unusual stereochemical course of epoxide rearrangement in a carvone-derived series [J].
Neef, G ;
Baesler, S ;
Depke, G ;
Vierhufe, H .
TETRAHEDRON LETTERS, 1999, 40 (45) :7969-7973
[47]   Copper-catalysed asymmetric conjugate addition of organometallic reagents to enones using S,O-ligands with a xylofuranose backbone [J].
Pàmies, O ;
Net, G ;
Ruiz, A ;
Claver, C ;
Woodward, S .
TETRAHEDRON-ASYMMETRY, 2000, 11 (04) :871-877
[48]   TITANIUM-INDUCED CONJUGATE ADDITION OF THE FLUORENONE DIANION TO ALPHA,BETA-ENONES [J].
PONS, JM ;
SANTELLI, M .
TETRAHEDRON LETTERS, 1982, 23 (47) :4937-4940
[49]   CONJUGATE ADDITION OF THE DIANION OF DIARYL KETONES TO ALPHA,BETA-ETHYLENIC KETONES PROMOTED BY TICL4-MG [J].
PONS, JM ;
SANTELLI, M .
TETRAHEDRON, 1990, 46 (02) :513-522
[50]   NEW CLASS OF MIXED CUPRATE(I) REAGENTS, HET(R)CULI, WHICH ALLOW SELECTIVE ALKYL GROUP TRANSFER [J].
POSNER, GH ;
WHITTEN, CE ;
STERLING, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (23) :7788-7800