Synthetic studies on apoptolidin: synthesis of the C1-C21 macrolide fragment

被引:46
作者
Toshima, K [1 ]
Arita, T [1 ]
Kato, K [1 ]
Tanaka, D [1 ]
Matsumura, S [1 ]
机构
[1] Keio Univ, Fac Sci & Technol, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan
关键词
apoptolidin; apoptosis; macrolide; macrocyclization;
D O I
10.1016/S0040-4039(01)01948-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereoselective and convergent synthesis of the C1-C21 macrocyclic segment. (2) of the apoptosis inducing macrolide antibiotic, apoptolidin (1), is described. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8873 / 8876
页数:4
相关论文
共 20 条
[1]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156
[2]   HYDROZIRCONATION .3. STEREOSPECIFIC AND REGIOSELECTIVE FUNCTIONALIZATION OF ALKYLACETYLENES VIA VINYLZIRCONIUM(IV) INTERMEDIATES [J].
HART, DW ;
BLACKBURN, TF ;
SCHWARTZ, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (03) :679-680
[3]   Structure of apoptolidin, a specific apoptosis inducer in transformed cells [J].
Hayakawa, Y ;
Kim, JW ;
Adachi, H ;
Shin-ya, K ;
Fujita, K ;
Seto, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (14) :3524-3525
[4]   RAPID ESTERIFICATION BY MEANS OF MIXED ANHYDRIDE AND ITS APPLICATION TO LARGE-RING LACTONIZATION [J].
INANAGA, J ;
HIRATA, K ;
SAEKI, H ;
KATSUKI, T ;
YAMAGUCHI, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (07) :1989-1993
[5]   A NOVEL AND EFFICIENT SYNTHESIS OF THE KEY INTERMEDIATE OF 1-BETA-METHYLCARBAPENEM ANTIBIOTICS FROM (S)-METHYL 3-HYDROXY-2-METHYLPROPIONATE [J].
KAWABATA, T ;
KIMURA, Y ;
ITO, Y ;
TERASHIMA, S ;
SASAKI, A ;
SUNAGAWA, M .
TETRAHEDRON LETTERS, 1986, 27 (51) :6241-6244
[6]   NEW ALLYLSTANNANES FOR THE CONNECTIVE CONSTRUCTION OF MONOPROTECTED VICINAL DIOLS [J].
KECK, GE ;
ABBOTT, DE ;
WILEY, MR .
TETRAHEDRON LETTERS, 1987, 28 (02) :139-142
[7]  
Kim JW, 1997, J ANTIBIOT, V50, P628
[8]   Synthesis of the macrocyclic core of apoptolidin [J].
Nicolaou, KC ;
Li, YW ;
Weyershausen, B ;
Wei, HX .
CHEMICAL COMMUNICATIONS, 2000, (04) :307-308
[9]   SPECIFIC REMOVAL OF ORTHO-METHOXYBENZYL PROTECTION BY DDQ OXIDATION [J].
OIKAWA, Y ;
YOSHIOKA, T ;
YONEMITSU, O .
TETRAHEDRON LETTERS, 1982, 23 (08) :885-888
[10]   Structure-activity relationships within a family of selectively cytotoxic macrolide natural products [J].
Salomon, AR ;
Zhang, YB ;
Seto, H ;
Khosla, C .
ORGANIC LETTERS, 2001, 3 (01) :57-59