Chiral base route to functionalised cyclopentenyl amines: formal synthesis of the cyclopentene core of nucleoside Q

• DOI: 10.1016/j.tetlet.2004.10.043
• Publication Date: 2004-11-06T18:03:10Z
• Authors: Sally J. Oxenford; Peter O’Brien; Mark R. Shipton
• Keywords: 01 natural sciences; 0104 chemical sciences

A chiral base route to a range of highly functionalised amino cyclopentenes has been developed. The key asymmetric step involved the chiral lithium amide base-mediated rearrangement of a protected trans-4-hydroxy cyclopentene oxide to give an allylic alcohol (88% ee). Subsequent Overman rearrangement gave a protected trans-1,2-aminocyclopentenol whereas Mitsunobu substitution with BocNHNs gave a protected cis-amino cyclopentenol. Both are proven intermediates for natural product synthesis. The protected cis-aminocyclopentenol was transformed in a few steps into a precursor of the cyclopentene core of nucleoside Q, a natural product whose deficiency in animals is related to tumour growth. © 2004 Elsevier Ltd. All rights reserved.