Asymmetric syntheses of (-)-isoretronecanol and (-)-trachelantamidine

Journal article

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.

Authors: Brambilla, M; Davies, S; Fletcher, A; Roberts, P; Thomson, J

• Publication status: Published
• Journal: TETRAHEDRON
• Volume: 70
• Issue: 2
• Pages: 204-211
• Publication date: 2014-01-14
• DOI: 10.1016/j.tet.2013.11.094
• EISSN: 1464-5416
• ISSN: 0040-4020
• Language: English
• Keywords: Asymmetric synthesis; Pyrrolizidine alkaloids; (-)-Trachelantamidine; (-)-Isoretronecanol; Lithium amide; Conjugate addition