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2005
Oxidation
O 0212
24- 049
Mild Protocols for Generating Molecular Complexity: A Comparative Study of
Hetero-Domino Reactions Based on the Oxidant and the Substitution Pattern. —
The previously described Pb(O-Ac)4-mediated oxidative cleavage—rearrangement of
bicyclic unsaturated 1,2-diols is reinvestigated applying Mn(O-Ac)3, Ph-I(O-Ac)2 or
Dess-Martin periodinane (DMP) as oxidant. However, oxidation with these oxidants
stops at the stage of tricyclic "half-cascade" intermediates like (II) while the complete
conversion toward oxabicycles like (IV) proceeds only with higher amounts of
Pb(O-Ac)4. Reactions with DMP are strongly influenced by the stereochemistry of the
starting diols (to be continued). — (CANDELA LENA, J. I.; SANCHEZ
FERNANDEZ, E. M.; RAMANI, A.; BIRLIRAKIS, N.; BARRERO, A. F.;
ARSENIYADIS*, S.; Eur. J. Org. Chem. 2005, 4, 683-pp; Inst. Chim. Subst. Nat.,
CNRS, F-91198 Gif-sur-Yvette, Fr.; Eng.) — Mischke
2005
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