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Total synthesis of natural spiro-trisindole enantiomers similisines A, B and their stereoisomers.

Authors :
Shi, Lunyong
Li, Lingyu
Wang, Jun
Huang, Bin
Zeng, Kewu
Jin, Hongwei
Zhang, Qingying
Jia, Yanxing
Source :
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. May2017, Vol. 58 Issue 20, p1934-1938. 5p.
Publication Year :
2017

Abstract

The first total synthesis of similisines A and B, a pair of unprecedented polybrominated spiro-trisindole enantiomers isolated from Laurencia similis , and their all stereoisomers had been accomplished in 6 steps from the known 5,6-dibromoindole. The described synthesis avoided any protecting-group manipulations, and the key all-carbon spirocenters were constructed via an intramolecular Friedel-Crafts cyclization. In addition, the rotamers of similisines and cytotoxic and NO production inhibitory activities of synthetic compounds were also discussed. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
00404039
Volume :
58
Issue :
20
Database :
Academic Search Index
Journal :
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
Publication Type :
Academic Journal
Accession number :
122698930
Full Text :
https://doi.org/10.1016/j.tetlet.2017.03.086