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An Efficient and General Method for the Stereodivergent Syntheses of Tadalafil‐Like Tetracyclic Compounds
Author(s) -
Xiao Sen,
Shi XiaoXin,
Ni Feng,
Xing Jing,
Yan JingJing,
Liu ShiLing
Publication year - 2010
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.200901378
Subject(s) - tadalafil , chemistry , epimer , stereochemistry , catalysis , deuterium , combinatorial chemistry , organic chemistry , medicine , sildenafil , physics , quantum mechanics
A clean and general DBU‐catalyzed epimerization at C‐12a position of the tadalafil‐like tetracyclic compounds has been fully studied. In addition, by using this clean epimerization as the key step, four stereomers of 6‐ d 1 ‐tadalafil were stereodivergently synthesized from both L ‐ and D ‐tryptophan methyl ester hydrochlorides and deuterated piperonal.