817210-72-3Relevant academic research and scientific papers
Chiral base route to functionalised cyclopentenyl amines: Formal synthesis of the cyclopentene core of nucleoside Q
Oxenford, Sally J.,O'Brien, Peter,Shipton, Mark R.
, p. 9053 - 9055 (2007/10/03)
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.
