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Intramolecular Alkynylogous Mukaiyama Aldol Reaction Starting from Bicyclic Alkanones Tethered to Alkynyl Esters: Formal Total Synthesis of (±)‐Hamigeran B |
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| Authors: | Laurence Miesch Dr. Tania Welsch Vincent Rietsch Michel Miesch Dr. |
| Affiliation: | Université de Strasbourg, Institut de Chimie, UMR 7177 CNRS/ULP, Laboratoire de Chimie Organique Synthétique, 1 rue Blaise Pascal, BP 296/R8, 67008 Strasbourg Cedex‐(France), Fax: (+33)?390‐24‐17‐54 |
| Abstract: | Selecting the ring : tert‐Butyldimethylsilyltriflate (TBSOTf)/NEt3 treatment of alkynyl esters tethered to bicycloalkanones leads to the formation of tricyclic allenoates with total diasteroselectivity at the ring junction. An intramolecular alkynylogous Mukaiyama aldol reaction promoted by a TBSOTf/NEt3 dual activation is involved. This novel methodology was illustrated by a formal total synthesis of (±)‐hamigeran B.  |
| Keywords: | aldol reaction allenes cascade reactions stereoselectivity total synthesis |