1375488-03-1Relevant articles and documents
Unexpected observations during the total synthesis of calothrixin B-sodium methoxide as a source of hydride
Bhosale, Shrikar M.,Momin, Aadil A.,Kunjir, Shrikant,Rajamohanan,Kusurkar, Radhika S.
, p. 155 - 162 (2014)
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. Temperature dependent NMR studies have been carried out for confirmation of the structure of one of the intermediates in the synthetic sequence.
An efficient total synthesis of calothrixin B
Bhosale, Shrikar M.,Gawade, Rupesh L.,Puranik, Vedavati G.,Kusurkar, Radhika S.
supporting information; experimental part, p. 2894 - 2896 (2012/07/27)
An efficient synthesis of calothrixin B (2) is demonstrated starting from 9H-carbazol-4-ol, having two one-pot reaction sequences as key steps. As a novel observation, DMF-methanol was shown to be a hydride donor for reduction of aldehyde to alcohol. Unexpectedly, nucleophilic substitution of benzyloxy by methoxy group was observed.
