New reagent for oxidative phenol coupling. The transformation of the monocyclic spermine base (S)-dihydroxyverbacine to the bicyclic alkaloid (S,S,S)-aphelandrine by cell free extract of barley seedlings

Citation
L. Nezbedova et al., New reagent for oxidative phenol coupling. The transformation of the monocyclic spermine base (S)-dihydroxyverbacine to the bicyclic alkaloid (S,S,S)-aphelandrine by cell free extract of barley seedlings, TETRAHEDR L, 42(25), 2001, pp. 4139-4141
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
25
Year of publication
2001
Pages
4139 - 4141
Database
ISI
SICI code
0040-4039(20010618)42:25<4139:NRFOPC>2.0.ZU;2-0
Abstract
The soluble protein fraction of barley seedlings (Hordeum vulgare, Graminea e) in the presence of O-2 stereoselectively catalyzes the intramolecular ph enol coupling of the monocyclic spermine base (S)-dihydroxyverbacine to the bicyclic aphelandrine in preparative yield. The expected microsomal-bond c ytochrome P-450 enzyme system does not contribute to this reaction. The nat ure of the involved biocatalyst still remains uncertain. The catalytic pote ntial of the cell free extract of barley seedlings suggests its possible us e as an efficient tool for large scale stereoselective chemoenzymatic synth esis of aphelandrine type alkaloids. (C) 2001 Elsevier Science Ltd. All rig hts reserved.