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

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• 作者：Shrikar M. Bhosale ; Aadil A. Momin ; Shrikant Kunjir ; P.R. Rajamohanan ; Radhika S. Kusurkar
• 关键词：Calothrixin B ; Sodium methoxide ; Sodium cyanoborohydride ; Reduction ; Azoxybenzene
• 刊名：Tetrahedron Letters
• 出版年：1 January, 2014
• 年：2014
• 卷：55
• 期：1
• 页码：155-162
• 全文大小：4592 K

文摘

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.