全功能化环C别秋水仙碱类化合物的汇聚合成。苯并环化方法。
Convergent synthesis of fully functionalized ring C allocolchicinoids. Benzannulation approach.
作者信息
Vorogushin A V, Wulff W D, Hansen H J
机构信息
Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
出版信息
Org Lett. 2001 Aug 23;3(17):2641-4. doi: 10.1021/ol0100881.
[reaction: see text]. A novel convergent approach to fully functionalized ring C allocolchicinoids is developed which is based on the benzannulation reaction of Fischer carbene complexes with alkynes. The efficacy of this strategy was established with the conversion of bromide 1a (R1 = Me, R2 = H) to the biaryl phenol 3a (R = Me, R(L) = Pr, R(S) = H) via the carbene complex 2a. Bromide 1b (R1 = t-Bu, R2 = OMe) was then used for the analogous preparation of the diastereomeric allocolchicinoids 3b (R = Me, R(L) = Pr, R(S) = H).
[反应：见正文]。开发了一种新颖的汇聚方法来合成完全官能化的环C别秋水仙碱类化合物，该方法基于费歇尔卡宾配合物与炔烃的苯并环化反应。通过卡宾配合物2a将溴化物1a（R1 = 甲基，R2 = 氢）转化为联芳基苯酚3a（R = 甲基，R(L) = 丙基，R(S) = 氢），证实了该策略的有效性。然后使用溴化物1b（R1 = 叔丁基，R2 = 甲氧基）类似地制备非对映异构的别秋水仙碱类化合物3b（R = 甲基，R(L) = 丙基，R(S) = 氢）。
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