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Org Lett. 2010 May 7;12(9):2084-7. doi: 10.1021/ol100574y.

The tert-butylsulfinamide lynchpin in transition-metal-mediated multiscaffold library synthesis.

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  • 1Tri-Institutional Training Program in Chemical Biology, Memorial Sloan-Kettering Cancer Center, 1275 York Avenue, Box 422, New York, New York 10065, USA.


A unified synthetic approach to diverse polycyclic scaffolds has been developed using transition-metal-mediated cycloaddition and cyclization reactions of enynes and diynes. The tert-butylsulfinamide group has been identified as a particularly versatile lynchpin in these reactions, with a reactivity profile uniquely suited for efficient, stereoselective substrate synthesis and downstream transformations. This approach provides 10 distinct, functionalized scaffold classes related to common core structures in alkaloid and terpenoid natural products.

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