Synthesis and Assignment of the Absolute Configuration of Indenotryptoline Bisindole Alkaloid BE-54017

被引：32

作者：

Kimura, Tomoyuki ^{[1
]}

Kanagaki, Shuhei ^{[2
]}

Matsui, Yusuke ^{[2
]}

Imoto, Masaya ^{[2
]}

Watanabe, Takumi ^{[1
]}

Shibasaki, Masakatsu ^{[1
]}

机构：

[1] Inst Microbial Chem, Shinagawa Ku, Tokyo 1410021, Japan

[2] Keio Univ, Dept Biosci & Informat, Fac Sci & Technol, Yokohama, Kanagawa 2238522, Japan

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 17期

关键词：

ISOGRANULATIMIDE ANALOGS; BIOLOGICAL-ACTIVITY; INHIBITORS; DIHYDROXYLATION; STAUROSPORINE; BIOSYNTHESIS; REBECCAMYCIN; PRODUCTS; OLEFINS;

D O I：

10.1021/ol3019314

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of the indenotryptoline bisindole alkaloid, BE-54017, was accomplished using osmium-promoted cis-dihydroxylation of maleimide as a key step. After optical resolution, the absolute configuration of this molecule was determined by comparing its optical otation and HPLC profile to those obtained for BE-54017 derived from enantiopure cladoniamide A, whose stereochemistry has been reported previously. BE-54017 with the correct absolute stereochemistry induced apoptosis of epidermal growth factor (EGF)-stimulated EGF receptor overexpressing A431 cells and inhibited vacuolar-type H+-ATPase (V-ATPase).

引用

页码：4418 / 4421

页数：4

共 50 条

[41] Assignment of absolute configuration to SCH 351448 via total synthesis
Cheung, Lael L.
Marumoto, Shinji
Anderson, Christopher D.
Rychnovsky, Scott D.
ORGANIC LETTERS, 2008, 10 (14) : 3101 - 3104
[42] (-)-Pseudodistomin E: First Asymmetric Synthesis and Absolute Configuration Assignment
Davies, Stephen G.
Fletcher, Ai M.
Roberts, Paul M.
Thomson, James E.
Zimmer, David
ORGANIC LETTERS, 2017, 19 (07) : 1638 - 1641
[43] Enantioselective Total Synthesis and Assignment of the Absolute Configuration of the Meroterpenoid (+)-Taondiol
Dethe, Dattatraya H.
Mahapatra, Samarpita
Sau, Susant Kumar
ORGANIC LETTERS, 2018, 20 (09) : 2766 - 2769
[44] Organocatalyzed asymmetric synthesis and absolute configuration assignment of enantioenriched α-benzylaminocoumarins
Lin, Hua
Tan, Yu
Wu, Jian-Ming
Yang, Xiao-Di
Chen, Jun-Hua
Sun, Xing-Wen
TETRAHEDRON LETTERS, 2015, 56 (07) : 913 - 917
[45] ABSOLUTE CONFIGURATION OF ALKALOID (+)SEDRIDINE AND OF (-)ALLOSEDRIDINE
BURTUILL.D
FODOR, G
HUBER, CS
LETOURNEAU, F
TETRAHEDRON, 1971, 27 (11) : 2055 - +
[46] STRUCTURE AND ABSOLUTE CONFIGURATION OF ALKALOID CLIVORINE
BIRNBAUM, KB
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL CRYSTALLOGRAPHY AND CRYSTAL CHEMISTRY, 1972, B 28 (SEP15): : 2825 - &
[47] MD-Based CD calculations for the assignment of the absolute axial configuration of the naphthylisoquinoline alkaloid dioncophylline A
Bringmann, G
Mühlbacher, J
Repges, C
Fleischhauer, J
JOURNAL OF COMPUTATIONAL CHEMISTRY, 2001, 22 (12) : 1273 - 1278
[48] Approach to the total synthesis of bisindole alkaloid-macralstonidine.
Zhao, S
Cook, JM
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 220 : U54 - U54
[49] First de novo synthesis of the bisindole alkaloid vinblastine
Schneider, C
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (22) : 4217 - 4219
[50] The first total synthesis of xenitorins B and C: assignment of absolute configuration
Chang, Wen-Sheng
Shia, Kak-Shan
Liu, Hsing-Jang
Ly, Tai Wei
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (20) : 3751 - 3753

← 1 2 3 4 5 →