Toward (-)-Enterocin: An Improved Cuprate Barbier Protocol To Overcome Strain and Sterical Hindrance
Antonio Rizzo1, Dirk Trauner1,2
1Department of Chemistry and Center for Integrated Protein Science , Ludwig-Maximilians-Universitat München , Butenandtstrasse 5-13 , 81377 München , Germany.
Abstract:
An approach toward (-)-enterocin, an antibiotic isolated from Streptomyces hygroscopicus, is described. Its compact, heavily oxidized protoadamantane core represents a daunting challenge for an efficient synthesis. Convergent assembly of its 2-oxabicyclo[3.3.1]nonane core with a cuprate-mediated Barbier reaction is disclosed. Its functionalization to a suitable substrate for a biomimetic aldol to close the final ring of the natural product is evaluated.
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