Alkynyliodonium Salts in Organic Synthesis. Application to the Total Synthesis of (−)-Agelastatin A and (−)-Agelastatin B
Journal of the American Chemical Society2002Vol. 124(31), pp. 9060–9061
Citations Over TimeTop 10% of 2002 papers
Abstract
The asymmetric total syntheses of (−)-agelastatin A and (−)-agelastatin B were accomplished in 14 steps each from (R)-epichlorohydrin. The pivotal transformation in both sequences was a sulfinate-promoted cyclization of an alkynyliodonium salt to furnish a key functionalized cyclopentene intermediate. Selective bromination in the final step led to either agelastatin A or agelastatin B, depending upon conditions.
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