A Simmons−Smith stereodefined procedure for the synthesis of cyclopropyl-1,2-bis(boronates) has been developed starting from the corresponding alkenes. The resulting compounds were then subjected to regioselective Suzuki−Miyaura couplings to produce diversely tri-or tetra-substituted arylcyclopropanes in good yields. Further functionalization with 2-lithiothiophene provided 1,2-bis(aryl)cyclopropanes. Article pubs.acs.org/joc
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The first total synthesis of recently isolated thiocladospolide A (1) and its C2-epimer have been achieved in nine straightforward linear steps with 12% of overall yield. The key feature of the synthesis is the construction of the macrocyclic ring via late stage ring-closing metathesis reaction followed by alkene reduction.
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