Synthesis of Strained 1,3-Diene Macrocycles via Copper-Mediated Castro–Stephens Coupling/Alkyne Reduction Tandem Reactions
2015
Li, Wei | Schneider, Christopher M. | Georg, Gunda I.
A copper-mediated macrocyclization involving the reaction of a vinyl iodide and a terminal alkyne followed by an in situ reduction of the enyne intermediate is reported. The reaction generates a conjugated Z-double bond within a strained medium-size lactone, lactam, or ether macrocycle. A variety of macrocyclic compounds bearing different ring sizes and functionalities were synthesized. A complementary stepwise procedure was also developed for less strained ring systems.
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