Concise Synthesis of PM-94128 and Y-05460M-A

被引:19
作者
Enomoto, Masaru [1 ]
Kuwahara, Shigefumi [1 ]
机构
[1] Tohoku Univ, Lab Appl Bioorgan Chem, Grad Sch Agr Sci, Aoba Ku, Sendai, Miyagi 9818555, Japan
关键词
BIOLOGICALLY-ACTIVE METABOLITES; MICROBIAL PRODUCTS; ISOCOUMARIN; DERIVATIVES;
D O I
10.1021/jo9014968
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantioselective total synthesis of PM-94128, a potent cytotoxin of microbial origin, was accomplished by a concise nine-step sequence of reactions in 14% overall yield from N-Boc-L-leucine. The synthesis of Y-05460M-A, a one-carbon lower homologue of PM-94128, was also achieved from N-BOC-L-valine by the same approach, which enabled its stereochemical determination.
引用
收藏
页码:7566 / 7569
页数:4
相关论文
共 20 条
[1]   Bioactive microbial metabolites Part 33.: Bacilosarcins A and B, novel bioactive isocoumarins with unusual heterocyclic cores from the marine-derived bacterium Bacillus subtilis [J].
Azumi, Miwa ;
Ogawa, Ken-ichi ;
Fujita, Tsuyoshi ;
Takeshita, Michinori ;
Yoshida, Ryuji ;
Furumai, Tamotsu ;
Igarashi, Yasuhiro .
TETRAHEDRON, 2008, 64 (27) :6420-6425
[2]   PM-94128, a new isocoumarin antitumor agent produced by a marine bacterium [J].
Canedo, LM ;
Puentes, JLF ;
Baz, JP .
JOURNAL OF ANTIBIOTICS, 1997, 50 (02) :175-176
[3]   Total Synthesis of Bacilosarcins A and B [J].
Enomoto, Masaru ;
Kuwahara, Shigefumi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (06) :1144-1148
[4]  
Gebhardt K, 2002, FEMS MICROBIOL LETT, V217, P199, DOI 10.1111/j.1574-6968.2002.tb11475.x
[5]   Sg17-1-4, a novel isocoumarin from a marine fungus Alternaria tenuis Sg17-1 [J].
Huang, Yong-Fu ;
Li, Lin-Hao ;
Tian, Li ;
Qiao, Li ;
Hua, Hui-Ming ;
Pei, Yue-Hu .
JOURNAL OF ANTIBIOTICS, 2006, 59 (06) :355-357
[6]   ISOLATION, PHYSICOCHEMICAL PROPERTIES AND BIOLOGICAL-ACTIVITIES OF AMICOUMACINS PRODUCED BY BACILLUS-PUMILUS [J].
ITOH, J ;
SHOMURA, T ;
OMOTO, S ;
MIYADO, S ;
YUDA, Y ;
SHIBATA, U ;
INOUYE, S .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1982, 46 (05) :1255-1259
[7]   AMICOUMACIN-A, A NEW ANTIBIOTIC WITH STRONG ANTI-INFLAMMATORY AND ANTI-ULCER ACTIVITY [J].
ITOH, J ;
OMOTO, S ;
SHOMURA, T ;
NISHIZAWA, N ;
MIYADO, S ;
YUDA, Y ;
SHIBATA, U ;
INOUYE, S .
JOURNAL OF ANTIBIOTICS, 1981, 34 (05) :611-613
[8]   STEREOSPECIFIC SYNTHESIS OF N-PROTECTED STATINE AND ITS ANALOGS VIA CHIRAL TETRAMIC ACID [J].
JOUIN, P ;
CASTRO, B ;
NISATO, D .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (06) :1177-1182
[9]  
Ma DW, 1996, TETRAHEDRON-ASYMMETR, V7, P2365
[10]   BIOLOGICALLY-ACTIVE METABOLITES FROM XENORHABDUS SPP .2. BENZOPYRAN-1-ONE DERIVATIVES WITH GASTROPROTECTIVE ACTIVITY [J].
MCINERNEY, BV ;
TAYLOR, WC ;
LACEY, MJ ;
AKHURST, RJ ;
GREGSON, RP .
JOURNAL OF NATURAL PRODUCTS, 1991, 54 (03) :785-795