Total synthesis of (+)-komaroviquinone

Heterocycles

Volumn 73, Issue C, 2007, Pages 227-235

  Majetich, George ^a   Yu, Jianhua ^a   Li, Yang ^a  

^a UNIVERSITY OF GEORGIA   (United States)

Author keywords

(+) Komaroviquinone; Aren's Reagent; Bromohydrin Formation; Cyclialkylation; Meyers Allylic Transposition

Indexed keywords

EID: 38349165504     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-07-S(U)37     Document Type: Article

References (34)

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7. For our synthesis of (±)-komaroviquinone, see the preceding manuscript.
8. The spectroscopic data obtained for all new compounds were fully consistent with the assigned structures. Reaction conditions have not been optimized. All yields are isolated yields.
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33. In related work, we have found that the C(l),C(10)-double bond of diene 12 readily isomerizes into conjugation with the C(6),C (7)-double bond upon exposure to either protic or Lewis acids. Thus in the first step, the oxidant adds to the C(I) carbon with migration of the double bond into the ring fusion (cf. 12ii).This intermediate is then further oxidized to generate conjugated dienone. {A figure is presented}
34. p3, R(1) = 0.0842 for 1721 observed reflections (I > 2 σ(I)). All non-hydrogen atoms were refined anisotropically. Hydrogen atoms were treated as idealized contributions. {A figure is presented}