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. ...

Related Articles:

Synthesis of the calothrixins, pentacyclic indolo [3, 2-j] phenanthridine alkaloids, using a biomimetic approach

[McErlean, Christopher S.P.; Sperry, Jonathan; Blake, Alexander J.; Moody, Christopher J. Tetrahedron, 2007 , vol. 63, # 45 p. 10963 - 10970]

Synthesis of the calothrixins, pentacyclic indolo [3, 2-j] phenanthridine alkaloids, using a biomimetic approach

[McErlean, Christopher S.P.; Sperry, Jonathan; Blake, Alexander J.; Moody, Christopher J. Tetrahedron, 2007 , vol. 63, # 45 p. 10963 - 10970]

Friedel-Crafts acylation and metalation strategies in the synthesis of calothrixins A and B

[Bernardo, Paul H.; Chai, Christina L. L. Journal of Organic Chemistry, 2003 , vol. 68, # 23 p. 8906 - 8909]

A biomimetic synthesis of the indolo [3, 2-j] phenanthridine alkaloid, calothrixin B

[Yamabuki, Akira; Fujinawa, Hikohito; Choshi, Tominari; Tohyama, Shigeo; Matsumoto, Kohji; Ohmura, Kana; Nobuhiro, Junko; Hibino, Satoshi Tetrahedron Letters, 2006 , vol. 47, # 33 p. 5859 - 5861]

Friedel-Crafts acylation and metalation strategies in the synthesis of calothrixins A and B

[Bernardo, Paul H.; Chai, Christina L. L. Journal of Organic Chemistry, 2003 , vol. 68, # 23 p. 8906 - 8909]

More Articles...