Synthesis of the C-13 side chain precursors of the 9-dihydrotaxane analogue ABT-271

被引:7
作者
Leanna, MR [1 ]
DeMattei, JA [1 ]
Li, WK [1 ]
Nichols, PJ [1 ]
Rasmussen, M [1 ]
Morton, HE [1 ]
机构
[1] Abbott Labs, Div Pharmaceut Prod, N Chicago, IL 60064 USA
关键词
D O I
10.1021/ol006508o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] N-Boc-L-Leucinol was converted to two C-13 side chain precursors of the 9-dihydrotaxane analogue ABT-271. The trans-oxazolidine acid 4 and the cis-Boc-lactam 2b were prepared in 44% and 40% overall yield, respectively, and with excellent (>98%) stereochemical purity.
引用
收藏
页码:3627 / 3630
页数:4
相关论文
共 25 条
[1]   THE UNCATALYZED RING-OPENING OF HETARYLOXIDES WITH NITROGEN NUCLEOPHILES - A DICHOTOMY OF REGIOSELECTIVITY [J].
ALCAIDE, B ;
BIURRUN, C ;
PLUMET, J ;
BORREDON, E .
TETRAHEDRON LETTERS, 1992, 33 (48) :7413-7416
[2]   PREPARATION OF ALPHA-METHYLENE AND ALPHA-ETHYLIDENE BETA-LACTAMS VIA THE ESTER ENOLATE IMINE CONDENSATION USING BETA-(DIALKYLAMINO) ESTERS AS STARTING MATERIALS - SCOPE AND SYNTHETIC APPLICATIONS [J].
ALCAIDE, B ;
ESTEBAN, G ;
MARTINCANTALEJO, Y ;
PLUMET, J ;
RODRIGUEZLOPEZ, J ;
MONGE, A ;
PEREZGARCIA, V .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (26) :7994-8002
[3]  
Boge T C., 1997, ENANTIOSELECTIVE SYN, P1
[4]   A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].
CARLSEN, PHJ ;
KATSUKI, T ;
MARTIN, VS ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938
[5]   IMPROVED PROTECTION AND ESTERIFICATION OF A PRECURSOR OF THE TAXOTERE(R) AND TAXOL SIDE-CHAINS [J].
COMMERCON, A ;
BEZARD, D ;
BERNARD, F ;
BOURZAT, JD .
TETRAHEDRON LETTERS, 1992, 33 (36) :5185-5188
[6]   A HIGHLY EFFICIENT, PRACTICAL APPROACH TO NATURAL TAXOL [J].
DENIS, JN ;
GREENE, AE ;
GUENARD, D ;
GUERITTEVOEGELEIN, F ;
MANGATAL, L ;
POTIER, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (17) :5917-5919
[7]  
DENIS JN, 1992, J ORG CHEM, V57, P4320
[8]   ISOLATION OF 9-DIHYDRO-13-ACETYLBACCATIN-III FROM TAXUS-CANADENSIS [J].
GUNAWARDANA, GP ;
PREMACHANDRAN, U ;
BURRES, NS ;
WHITTERN, DN ;
HENRY, R ;
SPANTON, S ;
MCALPINE, JB .
JOURNAL OF NATURAL PRODUCTS, 1992, 55 (11) :1686-1689
[9]  
HOLTON R, 1991, Patent No. 5015744
[10]  
LEANNA MR, 1992, TETRAHEDRON LETT, V33, P5029