Concise Preparation of the Bis-THF Core of Annonaceous Acetogenins

Abstract

A concise preparation of the all-(R) threo/trans/threo/ trans/threo bis-THF core present in natural acetogenins is presented. Starting from a terminal alkene, homometathesis and two consecutive stereoselective cyclizations afforded the bis-THF core through a short and efficient sequence. In addition, the isomeric erythro/trans/ threo/trans/erythro bis-THF core was also synthesized in high yield. The starting alkene was previously prepared from a homochiral cis-diol derived from biotransformation of bromobenzene.

Key words

annonaceous acetogenin - bis-THF - iodoetherification - enzymatic dihydroxylation

• References

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