Total synthesis of phoslactomycin B and its biosynthetic deamino precursor

被引:52
作者
Wang, Yong-Gang [1 ]
Takeyama, Ryuichi [1 ]
Kohayashi, Yuichi [1 ]
机构
[1] Tokyo Inst Technol, Dept Biomol Engn, Midori Ku, Yokohama, Kanagawa 2268501, Japan
关键词
asymmetric synthesis; natural products; phoslactomycins; phospholine; total synthesis;
D O I
10.1002/anie.200600458
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) The implicated intermediate in the biosynthesis of phospholine (phoslactomycin B, see picture), namely its deamino precursor, as well as phospholine itself are synthesized. The phoslactomycins show antitumor, antibacterial, and antifungal activities, however, it is not yet known which part of the skeleton contributes to the activities. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3320 / 3323
页数:4
相关论文
共 42 条
[1]   A QUICK PROCEDURE FOR THE PARTIAL REDUCTION OF TRIPLE BONDS [J].
AERSSENS, MHPJ ;
VANDERHEIDEN, R ;
HEUS, M ;
BRANDSMA, L .
SYNTHETIC COMMUNICATIONS, 1990, 20 (22) :3421-3425
[2]   NEW APPLICATIONS OF THE MITSUNOBU REACTION IN THE SYNTHESIS OF C-2 N-METHYL CARBAPENEMS [J].
ARNOULD, JC ;
LANDIER, F ;
PASQUET, MJ .
TETRAHEDRON LETTERS, 1992, 33 (47) :7133-7136
[3]   Total synthesis of fostriecin (CI-920) [J].
Boger, DL ;
Ichikawa, S ;
Zhong, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) :4161-4167
[4]   Fundamental role of the fostriecin unsaturated lactone and implications for selective protein phosphatase inhibition [J].
Buck, SB ;
Hardouin, C ;
Ichikawa, S ;
Soenen, DR ;
Gauss, CM ;
Hwang, I ;
Swingle, MR ;
Bonness, KM ;
Honkanen, RE ;
Boger, DL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (51) :15694-15695
[5]  
Chavez DE, 2001, ANGEW CHEM INT EDIT, V40, P3667, DOI 10.1002/1521-3773(20011001)40:19<3667::AID-ANIE3667>3.0.CO
[6]  
2-6
[7]  
Chavez DE, 2001, ANGEW CHEM, V113, P3779
[8]   Synthesis of the C1-C12 fragment of fostriecin [J].
Cossy, J ;
Pradaux, F ;
BouzBouz, S .
ORGANIC LETTERS, 2001, 3 (14) :2233-2235
[9]   Versatile enantiocontrolled synthesis of (+)-flostriecin [J].
Esumi, T ;
Okamoto, N ;
Hatakeyama, S .
CHEMICAL COMMUNICATIONS, 2002, (24) :3042-3043
[10]   TOTAL SYNTHESIS OF (+)-A83543A [(+)-LEPICIDIN-A] [J].
EVANS, DA ;
BLACK, WC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (11) :4497-4513