Synthesis of the tricyclic indole alkaloids, dilemmaones A and B

被引：5
作者：
Lambson, Katharine E. [1 ]
Dacko, Christopher A. [1 ]
McNeill, Jeffrey M. [1 ]
Akhmedov, Novruz G. [1 ]
Soderberg, Bjon C. G. [1 ]
机构：
[1] West Virginia Univ, C Eugene Bennett Dept Chem, Morgantown, WV 26506 USA
来源：
TETRAHEDRON | 2019年 / 75卷 / 49期
基金：
美国国家卫生研究院;
关键词：
PALLADIUM-CATALYZED SYNTHESIS; CIS-TRIKENTRIN; ABSOLUTE STRUCTURES; TRANS-TRIKENTRIN; O-NITROSTYRENES; (+/-)-CIS-TRIKENTRIN-A; SPONGE; RING; NITRATION; CONCISE;
D O I：
10.1016/j.tet.2019.130714
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Dilemmaones A-C are naturally occurring tricyclic indole alkaloids possessing a unique hydroxymethylene or methoxymethylene substituent at the C2 position of the indole core and a C6-C7 fused cyclopentanone. Dilemmaone B has been prepared in 5 steps from 5-methylindan-l-one, and dilemmaone A has been prepared in 3 steps from a common precursor, 6-bromo-5-methyl-7-nitroindan-1-one. In both syntheses, key steps include a Kosugi-Migita-Stille cross coupling and a reductive cyclization using hydrogen gas and a transition metal catalyst. (C) 2019 Elsevier Ltd. All rights reserved.
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页数：10
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