Stereoselective Synthesis of Piperidine Alkaloid (+)-α-Conhydrine and Its Pyrrolidine Analogue

Concise stereoselective syntheses of (+)‐α‐conhydrine and its pyrrolidine analogue are described. The key features are a highly diastereoselective chelation‐controlled hydride reduction of the amino ketone, to give the anti amino alcohol directly, and an intramolecular ring‐closing metathesis. Conci...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2012-11, Vol.1 (3), p.232-237
Main Authors: Jin, Tian, Mu, Yu, Kim, Gun-Woo, Kim, Sung-Soo, Kim, Jin-Seok, Huh, Sung-Il, Lee, Kee-Young, Joo, Jae-Eun, Ham, Won-Hun
Format: Article
Language:English
Subjects:
amino alcohols
conhydrine
natural products
pyrrolidines
ring-closing metathesis
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Summary:Concise stereoselective syntheses of (+)‐α‐conhydrine and its pyrrolidine analogue are described. The key features are a highly diastereoselective chelation‐controlled hydride reduction of the amino ketone, to give the anti amino alcohol directly, and an intramolecular ring‐closing metathesis. Concise stereoselective syntheses of (+)‐α‐conhydrine in 10 steps and 25 % overall yield and its pyrrolidine analogue in 9 steps and 36 % overall yield are described. The key features are a highly diastereoselective chelation‐controlled hydride reduction of the amino ketone to give the anti amino alcohol directly, and an intramolecular ring‐closing metathesis. Cbz=carboxybenzyl; TBS=tert‐butyldimethylsilyl.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201200065