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Heck–Matsuda Arylation as a Strategy to Access Kavalactones Isolated from Polygala sabulosa , Piper methysticum , and Analogues
Author(s) -
Soldi Cristian,
Moro Angélica V.,
Pizzolatti Moacir G.,
Correia Carlos R. D.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200308
Subject(s) - chemistry , moiety , heck reaction , olefin fiber , stereochemistry , organic chemistry , palladium , catalysis
Abstract Herein, we describe the total syntheses of three bioactive pyrones isolated from Polygala sabulosa (i.e., 1 , 4 , and 7 ) and eight isolated from Piper methysticum (i.e., 8 – 10 , 13 , 15 , and 18 – 20 ) using the Heck–Matsuda arylation as the key strategy. The evaluation of this methodology by employing different arenediazonium tetrafluoroborates revealed that the Heck arylation was more efficient when the olefin undergoing arylation possessed the vinyl‐2‐pyrone structural unit instead of the vinyl dihydro‐2‐pyrone moiety. The Heck–Matsuda arylation of many of the examined olefins proceeded in a practical manner with total regio‐ and stereocontrol.