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A Short, Catalytic, Asymmetric Synthesis of Diospongins A and B by a One‐Pot, Sequential Hetero‐Diels–Alder/Mukaiyama–Michael Reaction Process
Author(s) -
Anada Masahiro,
Washio Takuya,
Watanabe Yudai,
Takeda Koji,
Hashimoto Shunichi
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.201001125
Subject(s) - chemistry , enantioselective synthesis , catalysis , michael reaction , diels–alder reaction , organic chemistry , stereochemistry , combinatorial chemistry
A new route to the diarylheptanoid diospongins A and B was developed. The key step is a novel, one‐pot, sequential dirhodium(II) tetrakis[( S )‐3‐(benzo‐fused phthalimido)‐2‐piperidinonate] [Rh 2 ( S ‐BPTPI) 4 ] catalyzed enantioselective hetero‐Diels–Alder/TMSOTf‐catalyzed Mukaiyama–Michael reaction process. The sign of the optical rotation of natural diospongin B was determined to be (+) and not (–) as was originally reported.