Tetrahedron Letters p. 339 - 342 (1996)
Update date:2022-08-03
Topics:
Rychnovsky, Scott D.
Dahanukar, Vilas H.
On treatment with BF3 · OEt2 and TMSCN, epoxy ketone 1 cyclized to the bicyclic acetal 2, which then cleaved to give primarily the oxepane 5 as a single stereoisomer. Reductive decyanation of 5 led to the oxepane 7, a structural unit present in the brevetoxin family of natural products. The scope and limitations of this reaction sequence were investigated.
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