Title of article
Synthesis of vinca alkaloids and related compounds. Part 110: A new synthetic method for the preparation of pandoline-type alkaloid-like molecules
Author/Authors
Fl?ri?n T?th، نويسنده , , Julianna Ol?h، نويسنده , , Gy?rgy Kalaus، نويسنده , , Istv?n Greiner، نويسنده , , ?ron Sz?ll?sy، نويسنده , , ?gnes G?m?ry، نويسنده , , L?szl? Hazai، نويسنده , , Csaba Sz?ntay، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2008
Pages
7
From page
7949
To page
7955
Abstract
A practicable synthesis of a pandoline-type alkaloid-like molecule is reported through an efficient preparation of carbinolamine ether intermediates (9a and 9b). The key step of the synthesis consists of an intramolecular cycloaddition of the secodine-type intermediate (2), which was formed from the tryptamine derivative (3) and lactol (4). The mechanism of the cycloaddition reaction was investigated by quantum chemical calculations and it was found to follow a step-wise mechanism involving a zwitterionic intermediate (15). By employing this strategy, other members of the family of pandoline alkaloids or alkaloid-like molecules could be synthesized by reacting the tryptamine derivative with appropriately functionalized aldehydes.
Keywords
Pandoline , ?-Aspidospermane alkaloids , Diels–Alder reaction , Reaction mechanism , 19-Hydroxy-20-epipandoline , Pandoline-like molecule , 20-Epipandoline
Journal title
Tetrahedron
Serial Year
2008
Journal title
Tetrahedron
Record number
1094455
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