Concise and highly selective asymmetric synthesis of acosamine from sorbic acid

Journal article

Diastereoselective conjugate addition of lithium (R)-N-benzyl-N-(α- methylbenzyl)amide to tert-butyl sorbate and subsequent chemo- and diastereoselective ammonium-directed olefinic oxidation of the resultant conjugate addition product {tert-butyl (3S,αR)-3-[N-benzyl-N-(α- methylbenzyl)amino]hex-4-ene} have been used as the key steps in a concise and highly selective asymmetric synthesis of the 2,3,6-trideoxy-3-aminohexose l-acosamine. This sequence of two chemical operations allows rapid assembly of the molecular architecture and facilitates the de novo asymmetric synthesis of methyl N,O-diacetyl-α-l-acosaminide in only 7 steps from commercially available sorbic acid in 15% overall yield. © 2010 Elsevier Ltd. All rights reserved.

Authors: Bagal, S; Davies, S; Fletcher, A; Lee, J; Roberts, P

• Publication status: Published
• Journal: TETRAHEDRON LETTERS
• Volume: 52
• Issue: 17
• Pages: 2216-2220
• Publication date: 2011-04-27
• DOI: 10.1016/j.tetlet.2010.12.035
• ISSN: 0040-4039
• Language: English
• Keywords: 2,3,6-Trideoxy-3-aminohexose; Acosamine; Conjugate addition; Ammonium-directed olefinic oxidation