A Short, Catalytic, Asymmetric Synthesis of Diospongins A and B by a One‐Pot, Sequential Hetero‐Diels–Alder/Mukaiyama–Michael Reaction Process | Zendy

Anada Masahiro | Zendy; Washio Takuya | Zendy; Watanabe Yudai | Zendy; Takeda Koji | Zendy; Hashimoto Shunichi | Zendy

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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.

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