Tietze Lutz F, Zhou Yifa
Institut für Organische Chemie der Universität, Tammannstrasse 2, D-37077 Göttingen (Germany), Fax: (+49) 551-39-9476.
Angew Chem Int Ed Engl. 1999 Jul 12;38(13-14):2045-2047. doi: 10.1002/(SICI)1521-3773(19990712)38:13/14<2045::AID-ANIE2045>3.0.CO;2-U.
A very short reaction sequence consisting of a domino Knoevenagel/hetero-Diels-Alder reaction with subsequent solvolysis and hydrogenation, provides the indole alkaloid hirsutine, which greatly inhibits the growth of influenza A viruses, and related compounds in enantiomerically pure form (see reaction scheme). The facial differentiation of the cycloaddition can be reversed by simple variation of the substituents on the indole nitrogen atom (H/tBuOCO). Cbz=benzyloxycarbonyl.
一个非常短的反应序列，由多米诺Knoevenagel/杂环狄尔斯-阿尔德反应以及随后的溶剂解和氢化反应组成，可提供对映体纯形式的吲哚生物碱hirsutine及其相关化合物，该生物碱能极大地抑制甲型流感病毒的生长（见反应式）。通过简单改变吲哚氮原子上的取代基（H/tBuOCO），环加成反应的面选择性可以反转。Cbz = 苄氧羰基。
