TOTAL SYNTHESIS OF (+)-HITACHIMYCIN

被引:20
作者
SMITH, AB [1 ]
RANO, TA [1 ]
CHIDA, N [1 ]
SULIKOWSKI, GA [1 ]
机构
[1] UNIV PENN,MONELL CHEM SENSES CTR,PHILADELPHIA,PA 19104
关键词
D O I
10.1021/jo00291a005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of the macrocyclic antibiotic-antitumor agent (+)-hitachimycin (1) has been achieved via a convergent and efficient route (22 steps, 1.2% overall yield). The key transformation entailed a highly stereoselective, three-component coupling of (-)-5-methoxycyclopentenone (5) with a zincate derived from vinyl iodide 4a and aldehyde (-)-6. © 1990, American Chemical Society. All rights reserved.
引用
收藏
页码:1136 / 1138
页数:3
相关论文
共 37 条
[1]   PREPARATION OF MACROLIDES VIA WITTIG REACTION - TOTAL SYNTHESIS OF (-)-VERMICULINE [J].
BURRI, KF ;
CARDONE, RA ;
CHEN, WY ;
ROSEN, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (22) :7069-7071
[2]   CYCLOPENTENE-3,5-DIONE .4. REACTION WITH BROMINATING AGENTS AND WITH ETHANOL [J].
DEPUY, CH ;
ISAKS, M ;
THURN, RD .
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (03) :744-&
[3]   GAMMA-FUNCTIONAL VINYL GRIGNARD-REAGENTS .2. IODOLYSIS, ALKYLATION AND ARYLATION OF IODO-ALCOHOLS [J].
DUBOUDIN, JG ;
JOUSSEAUME, B ;
BONAKDAR, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1979, 168 (02) :227-232
[4]   ALDEHYDES AND KETONES FROM THIOACETALS [J].
FETIZON, M ;
JURION, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (07) :382-&
[5]   STUDIES DIRECTED TOWARD THE PREPARATION OF POLYENE MACROLIDE MIMICS [J].
FLOYD, DM ;
FRITZ, AW .
TETRAHEDRON LETTERS, 1981, 22 (30) :2847-2850
[6]   EFFICIENT SYNTHESES OF (+/-)-BETA-CUPARENONE - CONJUGATE ADDITION OF ORGANOZINC REAGENTS [J].
GREENE, AE ;
LANSARD, JP ;
LUCHE, JL ;
PETRIER, C .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (05) :931-932
[7]   ON THE SELECTIVITY OF DEPROTECTION OF BENZYL, MPM (4-METHOXYBENZYL) AND DMPM (3,4-DIMETHOXYBENZYL) PROTECTING GROUPS FOR HYDROXY FUNCTIONS [J].
HORITA, K ;
YOSHIOKA, T ;
TANAKA, T ;
OIKAWA, Y ;
YONEMITSU, O .
TETRAHEDRON, 1986, 42 (11) :3021-3028
[8]  
HUANG SL, 1978, SYNTHESIS-STUTTGART, P297
[9]   CLEAVAGE OF SULFONAMIDES WITH SODIUM NAPHTHALENE [J].
JI, S ;
GORTLER, LB ;
WARING, A ;
BATTISTI, A ;
BANK, S ;
CLOSSON, WD ;
WRIEDE, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (20) :5311-&
[10]   REGIOSPECIFIC 1,4-ADDITION WITH GRIGNARD-DERIVED MIXED TRIORGANOZINCATE REAGENTS [J].
KJONAAS, RA ;
HOFFER, RK .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (17) :4133-4135