THE CHEMISTRY OF CYCLIC TAUTOMERS OF TRYPTOPHAN - TOTAL SYNTHESIS OF (-(ENT)-PSEUDOPHRYNAMINOL())

Authors
CRICH D PAVLOVIC AB SAMY R
Citation
D. Crich et al., THE CHEMISTRY OF CYCLIC TAUTOMERS OF TRYPTOPHAN - TOTAL SYNTHESIS OF (-(ENT)-PSEUDOPHRYNAMINOL()), Tetrahedron, 51(23), 1995, pp. 6379-6384
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
23
Year of publication
1995
Pages
6379 - 6384
Database
ISI
SICI code
0040-4020(1995)51:23<6379:TCOCTO>2.0.ZU;2-I
Abstract
A diastereoselective synthesis of the unnatural (+)-enantiomer of the hexahydropyrroloindole alkaloid (-)-pseudophrynaminol (3), isolated fr om the skin of the Australian frog Pseudophryne coriacea, from a cycli c tautomer (1) of L-tryptophan, is described, The CD spectrum of the s ynthetic 3 is opposite in sign to that of the natural material enablin g the configuration of the natural product to be established as 3aS,8a R.