Premium
Development of an Alkaloid–Pyrone Annulation: Synthesis of Pleiomaltinine
Author(s) -
Ziegler Robert E.,
Tan ShinJowl,
Kam TohSeok,
Porco John A.
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201204093
Subject(s) - annulation , pyrone , alkaloid , indole alkaloid , stereochemistry , chemistry , organic chemistry , catalysis
Odd Couple : A method for the synthesis of alkaloid‐pyrones using a novel pyrone annulation of β‐carbolines and indoles with 3‐siloxy‐4‐pyrones is reported. The approach has enabled synthesis of the unusual alkaloid‐pyrone pleiomaltinine from the plant‐derived indole‐alkaloid pleiocarpamine (see Scheme; TBS= tert ‐butyldimethylsilyl).