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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 23, Number 5
BKCSDE 23(5)
May 20, 2002 

 
Title
Mn(III)-Mediated Radical Cyclization for D 1 -3-Octalone Synthesis
Author
Miai Lee, Jae-Deuk Yang, Moon-Soo Kim, Hye-Sun Jeon, Woonphil Baik, Sangho Koo
Keywords
D1-3-Octalone, Aldol reaction, Mn(OAc)3, Radical cyclization.
Abstract
An efficient and practical synthetic method of △1 -3-octalone, which is a versatile building block for thesyntheses of polycyclic compounds, has been developed. The dianion of ethyl acetoacetate reacts with cyclohexene-1-carboxaldehyde (3) to produce the aldol adduct 6, which then undergoes Mn(Ⅲ)-mediated radical cyclization followed by acetate elimination to give △1 -3-octalone 4. A detailed mechanistic insight of Mn(Ⅲ)-mediated cyclization of 6 has been disclosed.
Page
736 - 740
Full Text
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