Abstract
The total synthesis of marine sesquiterpene upial was achieved starting from d-mannitol via sequential Michael reaction of the lithium enolate of 5 with methyl (E,S)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-pentenoate ((E)- 6), fragmentation reaction of tricyclic compound 22 and samarium(II) iodide-induced cyclization of diformate 3.
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