Total Synthesis of (−)-Lepadiformine A Utilizing Hg(OTf)2‑Catalyzed Cycloisomerization Reaction

A cytotoxic marine alkaloid (−)-lepadiformine A (1) possesses a unique structure characterized by the trans-1-azadecalin AB ring system fused with the AC spiro-cyclic ring. In this research, we found that a cycloisomerization reaction from amino ynone 2 to a 1-azaspiro[4.5]­decane skeleton 3, corres...

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Bibliographic Details
Published in:Organic letters 2015-12, Vol.17 (23), p.5772-5775
Main Authors: Nishikawa, Keisuke, Kikuchi, Seiho, Ezaki, Shinnosuke, Koyama, Tomoyuki, Nokubo, Haruka, Kodama, Takeshi, Tachi, Yoshimitsu, Morimoto, Yoshiki
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Alkaloids - pharmacology
Animals
Catalysis
Cyclization
Marine Biology
Mesylates - chemistry
Molecular Structure
Stereoisomerism
Urochordata - chemistry
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Summary:A cytotoxic marine alkaloid (−)-lepadiformine A (1) possesses a unique structure characterized by the trans-1-azadecalin AB ring system fused with the AC spiro-cyclic ring. In this research, we found that a cycloisomerization reaction from amino ynone 2 to a 1-azaspiro[4.5]­decane skeleton 3, corresponding to the AC ring system of 1, is promoted by Hg­(OTf)2. Thus, we have accomplished the efficient total synthesis of (−)-lepadiformine A in 28% overall yield by featuring the novel Hg­(OTf)2-catalyzed cycloisomerization.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02867