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A facile and highly stereoselective synthesis of trichonine by two consecutive reactions of arsonium salts
Author(s) -
Shi Lilan,
Yang Jianhua,
Li Ming,
Huang YaoZeng
Publication year - 1988
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198819880411
Subject(s) - chemistry , potassium carbonate , bromide , stereoselectivity , potassium bromide , yield (engineering) , potassium , organic chemistry , medicinal chemistry , catalysis , materials science , metallurgy
Trichonine ( 5 ) has been synthesized from 1‐hexadecanal ( 1 ) by two steps of consecutive olefination, in which formylmethyltriphenylarsonium bromide ( 2 ) and (pyrrolidinecarbonyl)methyltriphenylarsonium bromide ( 4 ) were used in the presence of potassium carbonate. The product was obtained in pure (2 E ,4 E ) configuration, and the overall yield reached 87%.