Functionalized Phenanthridine and Dibenzopyranone Derivatives through Benzyne Cyclization – Application to the Total Syntheses of Trisphaeridine andN-Methylcrinasiadine
作者:Roberto Sanz、Yolanda Fernández、M. Pilar Castroviejo、Antonio Pérez、Francisco J. Fañanás
DOI:10.1002/ejoc.200600621
日期:2007.1
series of regioselectively functionalized benzo[c]chromen-6-ones, phenanthridinones, and phenanthridine derivatives have been prepared by an anionic cyclization and in situ oxidation sequence starting from 2-bromobenzyl-2-fluorophenyl ethers and amines. These processes involve the generation of a benzyne-tethered aryllithium intermediate and subsequent 6-exo-dig cyclization. By applying this methodology
从 2-溴苄基-2-氟苯基醚和胺开始,通过阴离子环化和原位氧化序列制备了一系列区域选择性功能化的苯并 [c] 色烯-6-酮、菲啶酮和菲啶衍生物。这些过程涉及苯炔系芳基锂中间体的生成和随后的 6-exo-dig 环化。通过将这种方法应用于合适的起始材料,石蒜科生物碱 trisphaeridine 和 N-methylcrinasiadine 的短而有效的合成已经以良好的总产率实现。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)