Banwell Martin G, Ma Xinghua, Taylor Rebecca M, Willis Anthony C
Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia.
Org Lett. 2006 Oct 12;8(21):4959-61. doi: 10.1021/ol062020x.
[reaction: see text] Reaction of N-methylindole (4) with 6,6-dibromobicyclo[3.1.0]hexane (5) in the presence of silver tetrafluoroborate affords conjugate 7 in 67% yield. This product can be readily elaborated to compounds 12b and 13b which embody the polycyclic frameworks associated with members of the hapalindole and fischerindole classes of alkaloids. The chiral-auxiliary-substituted 6,6-dibromobicyclo[3.1.0]hexanes 21 and 22 react with indole to give adducts likely to be useful in the enantioselective total synthesis of the title alkaloids.
[反应：见正文] N-甲基吲哚（4）与6,6-二溴双环[3.1.0]己烷（5）在四氟硼酸银存在下反应，以67%的产率得到共轭物7。该产物可容易地转化为化合物12b和13b，它们体现了与哈帕林多生物碱和费舍尔吲哚生物碱类成员相关的多环骨架。手性辅助取代的6,6-二溴双环[3.1.0]己烷21和22与吲哚反应，得到可能用于标题生物碱对映选择性全合成的加合物。
