Mild and efficient Lewis acid-promoted detritylation in the synthesis of N-hydroxy amides: a concise synthesis of (-)-Cobactin T.
An efficient, high-yielding Lewis acid promoted deprotection of O-trityl hydroxylamine derivatives is described. A range of acid-labile protecting groups, such as N-Boc and O-TBS, were tolerated under these mild conditions. The present method is applicable to the synthesis of a broad range of hydroxylamine derivatives, including N-hydroxy amides (hydroxamic acids), N-hydroxy sulfonamides, and N-hydroxy ureas, which often exhibit significant biological activities. An application of this methodology for a concise synthesis of (-)-Cobactin T (18) is also demonstrated.
Yang
Shyh-Ming
SM
Johnson & Johnson Pharmaceutical Research and Development, L.L.C. 8 Clarke Drive, Cranbury, New Jersey 08512, USA. syang9@prdus.jnj.com
Lagu
Bharat
B
Wilson
Lawrence J
LJ
D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D006877:Hydroxamic Acids / Q000737:chemistry; D006898:Hydroxylamines / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D014320:Triphenylmethyl Compounds / Q000737:chemistry*
D001381:Azepines; D006877:Hydroxamic Acids; D006898:Hydroxylamines; D007202:Indicators and Reagents; D014320:Triphenylmethyl Compounds; C524936:cobactin T