EXPEDIENT SYNTHESES OF (+)-CIS-(2R,3S)-3-HYDROXYPROLINE AND (-)-(1S,5S)-2-OXA-6-AZABICYCLO[3.3.0]OCTAN-3-ONE (THE GEISSMAN-WAISS LACTONE) - FORMAL ENANTIOSELECTIVE SYNTHESES OF (-)-RETRONECINE AND RELATED PYRROLIZIDINE ALKALOIDS

被引:47
作者
COOPER, J
GALLAGHER, PT
KNIGHT, DW
机构
[1] CHEM DEPT,UNIV PK,NOTTINGHAM NG7 2RD,ENGLAND
[2] LILLY RES CTR LTD,WINDLESHAM GU20 6PH,SURREY,ENGLAND
关键词
D O I
10.1039/c39880000509
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:509 / 510
页数:2
相关论文
共 22 条
[1]  
ATAL CK, 1978, LLOYDIA, V41, P312
[2]   3-PYRROLIDINONES BY INTRAMOLECULAR CONDENSATION [J].
BLAKE, J ;
RAPOPORT, H ;
WILLSON, CD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (23) :5293-&
[3]   AN ENANTIOSPECIFIC SYNTHESIS OF (+)-RETRONECINE AND RELATED ALKALOIDS [J].
BUCHANAN, JG ;
SINGH, G ;
WIGHTMAN, RH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (19) :1299-1300
[4]   RECENT ADVANCES IN THE USE OF ENZYME-CATALYZED REACTIONS IN ORGANIC RESEARCH - THE SYNTHESIS OF BIOLOGICALLY-ACTIVE NATURAL-PRODUCTS AND ANALOGS [J].
BUTT, S ;
ROBERTS, SM .
NATURAL PRODUCT REPORTS, 1986, 3 (05) :489-503
[5]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[6]   PMR SPECTRA OF 1,2-SUBSTITUTED PROLINES [J].
GALLINA, C ;
VIGLINO, P ;
PACI, M .
OMR-ORGANIC MAGNETIC RESONANCE, 1972, 4 (01) :31-&
[7]   TOTAL SYNTHESIS OF (+)-RETRONECINE [J].
GEISSMAN, TA ;
WAISS, AC .
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (01) :139-&
[8]   SEMI-SYNTHETIC PYRROLIZIDINE ALKALOID ANTI-TUMOR AGENTS [J].
GELBAUM, LT ;
GORDON, MM ;
MILES, M ;
ZALKOW, LH .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (13) :2501-2504
[9]  
HAUSLER J, 1983, LIEBIGS ANN CHEM, P982
[10]  
Morita K., 1963, J AM CHEM SOC, V85, P2832