HIPPEASTRINE SYNTHESIS - A COMBINED BIO-DIOXYGENATION ORGANOIRON CHIRALITY RELAY APPROACH

被引:15
作者
ASTLEY, ST [1 ]
MEYER, M [1 ]
STEPHENSON, GR [1 ]
机构
[1] UNIV E ANGLIA,SCH CHEM SCI,NORWICH NR4 7TJ,NORFOLK,ENGLAND
关键词
D O I
10.1016/S0040-4039(00)60339-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The regio- and enantioselective preparation of tricarbonyl(eta5-6(S)-endo-methoxy-1(S)-ethoxycyclohexadienyl)iron(1+) hexafluorophosphate(1-) (3, R = OEt), via a biotransformation entry, is described. The optical purity of 3 (R = OEt), which is required as an intermediate for hippeastrine synthesis, was found to be > 98% e.e. by an NMR chiral shift method.
引用
收藏
页码:2035 / 2038
页数:4
相关论文
共 20 条
[11]  
MARTIN SF, 1987, ALKALOIDS, V30, P289
[12]   ORGANOIRON COMPLEXES IN ORGANIC-SYNTHESIS .21. METHODS FOR CONTROLLING THE REGIOSELECTIVITY OF NUCLEOPHILE ADDITION TO "TRICARBONYL(CYCLOHEXADIENYLIUM)IRON COMPLEXES [J].
PEARSON, AJ ;
HAM, P ;
CHI, WO ;
PERRIOR, TR ;
REES, DC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (07) :1527-1534
[13]   PREPARATION OF OPTICALLY PURE TRICARBONYLCYCLOHEXADIENYLIRON COMPLEXES - USE OF A TRIFLUOROMETHYL GROUP AS A REGIODIRECTOR DURING HYDRIDE ABSTRACTION [J].
PEARSON, AJ ;
GELORMINI, AM ;
PINKERTON, AA .
ORGANOMETALLICS, 1992, 11 (02) :936-938
[16]   COMPLEMENTARY REGIOSELECTION IN NUCLEOPHILE ADDITIONS TO CATIONIC ETA-5-CYCLOHEXADIENYL IRON COMPLEXES [J].
STEPHENSON, GR ;
HOWARD, PW ;
OWEN, DA ;
WHITEHEAD, AJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (09) :641-642
[17]   ASSIGNMENT OF ABSOLUTE-CONFIGURATIONS FROM THE CIRCULAR-DICHROISM SPECTRA OF CYCLIC ETA-4-DIENE COMPLEXES OF FE(CO)3 [J].
STEPHENSON, GR ;
HOWARD, PW ;
TAYLOR, SC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (02) :127-129
[18]   REGIOSELECTIVE ACCESS TO TRICARBONYLIRON COMPLEXES - CONTROLLED PREPARATION AND REACTIONS OF TRIFLUOROMETHYL-SUBSTITUTED COMPLEXES [J].
STEPHENSON, GR ;
HOWARD, PW ;
TAYLOR, SC .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 419 (1-2) :C14-C17
[19]  
STEPHENSON GR, 1990, TETRAHEDRON LETT, V31, P3979
[20]   PI-COMPLEXES WITH PLANAR CHIRALITY - CONTROL CENTERS FOR STEREOSELECTIVE SYNTHESIS [J].
STEPHENSON, GR ;
ALEXANDER, RP ;
MORLEY, C ;
HOWARD, PW .
PHILOSOPHICAL TRANSACTIONS OF THE ROYAL SOCIETY A-MATHEMATICAL PHYSICAL AND ENGINEERING SCIENCES, 1988, 326 (1592) :545-556