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A Four-Step Synthesis of (±)-γ-Lycorane via Pd0-Catalyzed Double C(sp2)–H/C(sp3)–H Arylation
Organic Letters ( IF 5.2 ) Pub Date : 2018-01-18 00:00:00 , DOI: 10.1021/acs.orglett.7b03909
Ronan Rocaboy 1 , David Dailler 1 , Olivier Baudoin 1
Affiliation  

An expedient synthesis of lycorine alkaloids is reported using a palladium(0)-catalyzed double C–X/C–H arylation as the key step. The selectivity of this reaction was controlled through the judicious choice of the two halogen atoms, and its generality was demonstrated through the construction of various substituted pyrrolophenanthridinones. A selective arene hydrogenation allowed for the completion of the synthesis of (±)-γ-lycorane in just four steps from commercially available precursors.

中文翻译:

Pd 0催化双C(sp 2)–H / C(sp 3)–H芳基化四步合成(±)-γ-环烷

据报道,使用钯(0)催化的双CX / CH芳基化作为关键步骤,可以方便地合成丝氨酸碱生物碱。通过明智地选择两个卤素原子来控制该反应的选择性,并通过构建各种取代的吡咯并菲基蒽酮来证明其一般性。选择性的芳烃加氢仅需四个步骤即可完成从市售前体的合成(±)-γ-番石榴烷。
更新日期:2018-01-18
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