Total Synthesis and Structure Revision of Diplobifuranylone B.

ABSTRACT: An asymmetric total synthesis of diplobifuranylone B was achieved in 10 steps for the longest linear sequence and in 15.8% overall yield from commercially available methyl (R)-(+)-lactate and l-glutamic acid. This synthesis features a stereoselective construction of the key 2,5-dihydrofuran ring in the natural product via a recently developed asymmetric gold catalysis. The stereochemical flexibility offered by the catalysis enables an expedient revision of the reported structure of diplobifuranylone B, where the relative stereochemistry of the 2,5-dihydrofuran moiety was previously misassigned as cis instead of trans.

SUBMITTER: Cheng X 

PROVIDER: S-EPMC7386208 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature