Unexpected observations during the total synthesis of calothrixin B–sodium methoxide as a source of hydride

…, AA Momin, S Kunjir, PR Rajamohanan, RS Kusurkar

Index: Bhosale, Shrikar M.; Momin, Aadil A.; Kunjir, Shrikant; Rajamohanan; Kusurkar, Radhika S. Tetrahedron Letters, 2014 , vol. 55, # 1 p. 155 - 162

Full Text: HTML

Citation Number: 8

Abstract

Abstract During the total synthesis of calothrixin B, various novel and unexpected results were noticed such as cleavage of C–N bond in imine using sodium cyanoborohydride, sodium methoxide as a hydride source for reduction, deformylation in the presence of bromine, and deacylation using ceric ammonium nitrate (CAN). A detailed mechanism has been proposed for the unexpected results and a few of them are generalized. ...