Harmata Michael, Hong Xuechuan, Barnes Charles L
Department of Chemistry, University of Missouri-Columbia, Columbia, Missouri 65211, USA.
Org Lett. 2004 Jun 24;6(13):2201-3. doi: 10.1021/ol049334+.
[reaction: see text] The tricyclic benzothiazine 15 was prepared in a straightforward fashion via a completely stereoselective intramolecular Friedel-Crafts alkylation. This compound represents a potential precursor to the antitubercular agent, pseudopteroxazole. Its synthesis proceeded via a completely selective, intramolecular addition of a sulfoximine-stabilized carbanion to an alpha,beta-unsaturated ester, followed by functional group manipulations.
[反应:见正文] 三环苯并噻嗪15通过完全立体选择性的分子内傅克烷基化以直接的方式制备。该化合物是抗结核药物假蕨素唑的潜在前体。其合成过程是通过亚磺酰亚胺稳定的碳负离子向α,β-不饱和酯进行完全选择性的分子内加成,然后进行官能团操作。