The chemistry of indoles part 91 - Preparations of melatonin and 1-hydroxymelatonin, and its novel nucleophilic dimerization to (+/-)-3a,3a '-bispyrrolo[2,3-b]indoles

Authors
Somei, M Oshikiri, N Hasegawa, M Yamada, F
Citation
M. Somei et al., The chemistry of indoles part 91 - Preparations of melatonin and 1-hydroxymelatonin, and its novel nucleophilic dimerization to (+/-)-3a,3a '-bispyrrolo[2,3-b]indoles, HETEROCYCLE, 51(6), 1999, pp. 1237
Citations number
28
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
51
Issue
6
Year of publication
1999
Database
ISI
SICI code
0385-5414(19990601)51:6<1237:TCOIP9>2.0.ZU;2-0
Abstract
A unique synthetic method for melatonin was established through biologicall y promising synthetic intermediates, 1-Hydroxymelatonin was prepared as cry stals for the first time. It reacted with 85% formic acid to give (+/-)-3a, 3a'-bispyrrolo[2,3-b]indole compound, whose structure was unequivocally det ermined by X-Ray crystallographic analysis.