174063-70-8Relevant articles and documents
Oxepanes from an unusual acetal cleavage of 6,8-dioxabicyclo[3.2.1]octanes
Rychnovsky, Scott D.,Dahanukar, Vilas H.
, p. 339 - 342 (1996)
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.