Organic Letters
Organic Letters
5 years ago

Total Synthesis of (−)-Angiopterlactone B

Total Synthesis of (−)-Angiopterlactone B
Gary S. Nichol, Andrew L. Lawrence, Marie I. Thomson
An enantioselective total synthesis of (−)-angiopterlactone B has been accomplished in four steps. The synthesis features a proposed biomimetic domino ring-contraction/oxa-Michael/Michael dimerization sequence, forming three new bonds, two new rings, and three new contiguous stereogenic centers in a single step. It has been determined that the originally proposed absolute configuration of natural (+)-angiopterlactone B needs revision. This reveals that angiopteroside, a known glycoside natural product, is the likely biosynthetic precursor to (+)-angiopterlactone B.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00929

DOI: 10.1021/acs.orglett.7b00929

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