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A total synthesis of the aglycone of IB-00208 was accomplished in 22 steps using a newly developed approach towards polycyclic 1,4-dioxygenated xanthones from benzocyclobutenones. The generality of this entry to xanthones was initially established on several model systems before it was successfully applied to the construction of the hexacyclic core of the natural product. A new and potentially general...
A two-step procedure is described to access 3-alkoxycyclobutanones from chloroacetyl chloride utilizing a step-wise [2+2] ketene cycloaddition followed by catalytic hydrogenation to reduce the α-chlorine in a single reaction sequence. The resulting cyclobutanones can be readily converted into a variety of cis or trans-1,3-disubstituted aminocyclobutanols and cyclobutanediols.
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