EFFICIENT SYNTHESES OF PROTECTED (2S,3S)-2,3-BIS(HYDROXYMETHYL)CYCLOBUTANONE, KEY INTERMEDIATES FOR THE SYNTHESIS OF CHIRAL CARBOCYCLIC ANALOGS OF OXETANOCIN

被引:44
作者
HSIAO, CN
HANNICK, SM
机构
[1] Abbott Laboratories, Process Chemistry, Pharmaceutical Products Division Abbott Park
关键词
D O I
10.1016/S0040-4039(00)97127-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Protected forms of (2S,3S)-2,3-bis(hydroxymethyl)cyclobutanone, key intermediates for the synthesis of chiral carbocyclic oxetanocin analogues, were prepared from Feist's acid. © 1990.
引用
收藏
页码:6609 / 6612
页数:4
相关论文
共 19 条
[1]   SYNTHESIS OF CYCLOPROPANE DERIVATIVES - PRECURSORS FOR DIMETHYLENECYCLOPROPANE AND TRIMETHYLENECYCLOPROPANE [J].
BLOMQUIST, AT ;
LONGONE, DT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (08) :2012-2017
[2]  
DOERING WVE, 1970, TETRAHEDRON, V26, P2825
[3]  
FEIST F, 1893, CHEM BER, V26, P747
[4]  
HONJO M, 1989, CHEM PHARM BULL, V37, P1413
[5]   1-(PHENYLSULFONYL)-2-(TRIMETHYLSILYL)ETHANE - A VALUABLE INTERMEDIATE FOR SYNTHESIS OF OLEFINS, ALLYLTRIMETHYLSILANES, BETA-TRIMETHYLSILYL KETONES, VINYL SULFONES, 2-(PHENYLSULFONYL)ALLYL ALCOHOLS, AND VARIED TRIMETHYLSILYL DERIVATIVES [J].
HSIAO, CN ;
SHECHTER, H .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (12) :2688-2699
[6]  
HSIAO CN, 1982, TETRAHEDRON LETT, P1963
[7]   ENANTIO-SELECTIVE AND DIASTEREO-SELECTIVE SYNTHESIS OF CARBOCYCLIC OXETANOCIN ANALOGS [J].
ICHIKAWA, Y ;
NARITA, A ;
SHIOZAWA, A ;
HAYASHI, Y ;
NARASAKA, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (24) :1919-1921
[8]   A SYNTHESIS OF MOENOCINOL [J].
KOCIENSKI, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (10) :2037-2039
[9]   THE X-RAY STRUCTURE DETERMINATION OF OXETANOCIN [J].
NAKAMURA, H ;
HASEGAWA, S ;
SHIMADA, N ;
FUJII, A ;
TAKITA, T ;
IITAKA, Y .
JOURNAL OF ANTIBIOTICS, 1986, 39 (11) :1626-1629
[10]   TOTAL SYNTHESIS OF IONOPHORE ANTIBIOTIC X-14547A [J].
NICOLAOU, KC ;
PAPAHATJIS, DP ;
CLAREMON, DA ;
MAGOLDA, RL ;
DOLLE, RE .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1440-1456