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Org Lett
; 22(11): 4118-4122, 2020 06 05.
Artigo
em Inglês
| MEDLINE
| ID: mdl-32383609
RESUMO
A stereocontrolled synthesis of 28, the C(10)-C(25) component of amphidinolide C (1), has been efficiently achieved. Reaction of the dithiane component 21 with nonracemic bis(epoxide) 19 directly affords functionalized 2,5-trans-disubstituted tetrahydrofuran 22. Propargylation is highly diastereoselective for the formation of the desired C(12)-C(13) anti stereochemistry, and the resulting terminal alkyne 25 is utilized for a regioselective syn-silylstannylation. A general strategy is illustrated for sequential replacement of stannyl and silyl substituents of the trisubstituted alkene to yield (E)-alkenyl iodide 28.