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Short and concise total asymmetric syntheses of (-)-isoretronecanol and (-)-trachelantamidine are reported. Oxidative cleavage of tert-butyl (S,S,S,Z)-7-[N-benzyl-N-(α-methylbenzyl)amino]cyclohept-3-ene-1- carboxylate, followed by hydrogenolysis promoted in situ cyclisation/reduction, which provided rapid access to the bicyclic core within (-)-isoretronecanol. Analogous treatment of the C(1)-epimer gave (-)-trachelantamidine. Overall, the syntheses of (-)-isoretronecanol and (-)-trachelantamidine were completed in eight and seven steps and 20 and 9.5% yield, respectively, from commercially available starting materials. © 2013 Elsevier Ltd. All rights reserved.

Original publication

DOI

10.1016/j.tet.2013.11.094

Type

Journal article

Journal

Tetrahedron

Publication Date

14/01/2014

Volume

70

Pages

204 - 211