Synthesis, Table of Contents Synthesis 2012; 44(23): 3639-3648DOI: 10.1055/s-0032-1316805 paper © Georg Thieme Verlag Stuttgart · New YorkStereo- and Regioselective Synthesis of 2-Amino-3,5-diols via Stereospecific Crotyl Transfer and Regioselective Aminohydroxylation Authors Author Affiliations Frank E. McDonald* Department of Chemistry, Emory University, Atlanta, GA 30322, USA Fax: +1(404)7276586 Email: fmcdona@emory.edu Claney L. Pereira Department of Chemistry, Emory University, Atlanta, GA 30322, USA Fax: +1(404)7276586 Email: fmcdona@emory.edu Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract A short synthesis of 2-amino-3,5-diols is described, including the all-S isomer enigmol, a synthetic anticancer compound inspired by the structure of fumonisin B1. The synthetic route features 1) stereospecific crotyl transfer to tetradecanal via pericyclic oxonia-Cope rearrangement; 2) stereoselective epoxidation of the alkene; 3) regioselective epoxide opening with azide; and 4) reduction of azide to amine. This manuscript also corrects a structure assignment error in a previously reported synthesis of one of the diastereomers of enigmol. Key words Key wordsallylation - rearrangement - regioselectivity - sphingolipids - stereoselective synthesis Full Text References References 1 Bezuidenhout SC, Gelderblom WC. A, Gorst-Allman CP, Horak RM, Marasas WF. O, Spiteller G, Vleggaar R. J. Chem. Soc., Chem. Commun. 1988; 743 2 Stockmann-Juvala H, Savolainen K. Human Exp. Toxicol. 2008; 27: 799 3a Humpf H.-U, Schmelz EM, Meredith FI, Vesper H, Vales TR, Wang E, Menaldino DS, Liotta DC, Merrill AH. J. Biol. Chem. 1998; 273: 19060 3b Seiferlein M, Humpf H.-U, Voss KA, Sullards MC, Allegood JC, Wang E, Merrill AH. Mol. Nutr. 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