biostudies-literatureGao DNIGMS NIH HHS3752-5https://www.ebi.ac.uk/biostudies/studies/S-EPMC2929272biostudies-literatureUnknown12(17)A total synthesis of the fostriecin has been achieved in 24 steps from enyne 11. The lactone moiety was installed by a Leighton allylation and Grubbs ring-closing metathesis reaction. The highly reactive Z,Z,E-triene moiety was installed via a late-stage Suzuki-Miyaura cross-coupling of a remarkably stable Z-vinyl boronate. The relative and absolute stereocenters of the C-8,9,11 triol were generated with a regio- and stereoselective asymmetric hydration/oxidation sequence.Organic lettersTotal synthesis of fostriecin: via a regio- and stereoselective polyene hydration, oxidation, and hydroboration sequence.PMC2929272R01 GM088839R01 GM088839-01A1R01 GM090259R01 GM088839-02GM088839O'Doherty GAGao DfalseTotal synthesis of fostriecin: via a regio- and stereoselective polyene hydration, oxidation, and hydroboration sequence.A total synthesis of the fostriecin has been achieved in 24 steps from enyne 11. The lactone moiety was installed by a Leighton allylation and Grubbs ring-closing metathesis reaction. The highly reactive Z,Z,E-triene moiety was installed via a late-stage Suzuki-Miyaura cross-coupling of a remarkably stable Z-vinyl boronate. The relative and absolute stereocenters of the C-8,9,11 triol were generated with a regio- and stereoselective asymmetric hydration/oxidation sequence.2010-01-01T00:00:00Z2010 Sep2024-11-20T04:47:29.534Z2019-03-27T00:33:39ZS-EPMC29292722068758510.1021/ol101340n