The development of tandem reactions based upon a zinc carbenoid-mediated homologation reaction provides access to spiroketals systems found in a variety of natural products.  Application of a tandem homologation-acylation reaction is used to establish four stereocenters found in in the papyracillic acid A, a spirolactone-containing system.  Development of a tandem homologation-aldol reaction provides access to an advanced intermediate in the synthesis of CJ-12,954, a spiroketal natural product with anti-helicobacter activity.

Formation of spiroketal systems through tandem zinc carbenoid-mediated homologation reactions

247th National Meeting (2014)

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