Expedient and Diastereodivergent Assembly of Terpenoid Decalin Subunits having Quaternary Stereocenters through Organocatalytic Robinson Annulation of Nazarov Reagent

Berkes Barbara; Ozsvath Kristof; Molnar Laura; Gati Tamas; Holczbauer Tamas; Kardos Gyorgy; Soos Tibor

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Expedient and Diastereodivergent Assembly of Terpenoid Decalin Subunits having Quaternary Stereocenters through Organocatalytic Robinson Annulation of Nazarov Reagent

机译：通过Nazarov试剂的有机催化Robinson环环法合成具有四级立体中心的萜烯十氢化萘亚基的便利和非对映异构体组装

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We report an expedient approach to highly functionalized cis- and trans-decalines that could function as key structural subunits toward the synthesis of various classes of terpenoids. Key to the strategy is an organocatalyzed Robinson annulation reaction of the Nazarov reagent that affords chiral enone building blocks with high enantioselectivities. The quaternary carbon stereogenic center can direct the subsequent reactions and allow the rapid and diastereoconvergent assembly of complex decalines with contiguous stereocenters.

机译：我们报告了权宜之计的高度功能化的顺式和反式癸烷，可以用作合成各种类萜类化合物的关键结构亚基。该策略的关键是Nazarov试剂的有机催化Robinson环化反应，该反应可提供具有高对映选择性的手性烯酮结构单元。季碳立体生成中心可以指导后续反应，并允许快速，非对映地组装具有连续立体中心的复杂十氢化萘。

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《Chemistry: A European journal》 |2016年第50期|共6页
作者
Berkes Barbara; Ozsvath Kristof; Molnar Laura; Gati Tamas; Holczbauer Tamas; Kardos Gyorgy; Soos Tibor;
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正文语种 eng
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asymmetric synthesis; diastereoselectivity; fused-ring systems; organocatalysis; terpenoids;

机译：不对称合成;非对映选择性;稠环系统;有机催化;萜类化合物;

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1. Expedient and Diastereodivergent Assembly of Terpenoid Decalin Subunits having Quaternary Stereocenters through Organocatalytic Robinson Annulation of Nazarov Reagent [J] . Berkes Barbara, Ozsvath Kristof, Molnar Laura, Chemistry: A European journal . 2016,第50期

机译：通过Nazarov试剂的有机催化Robinson环环法合成具有四级立体中心的萜烯十氢化萘亚基的便利和非对映异构体组装
2. Solid-phase synthesis of decalin scaffolds by Robinson annulation with immobilised Nazarov reagents [J] . Rottger S, Waldmann H European journal of organic chemistry . 2006,第9期

机译：固定化Nazarov试剂通过Robinson环化固相合成萘烷骨架
3. Toward the total synthesis of palhinine A: Expedient assembly of multifunctionalized isotwistane ring system with contiguous quaternary stereocenters [J] . Zhang G.-B., Wang F.-X., Du J.-Y., Organic letters . 2012,第14期

机译：迈向巴勒斯坦甲胺的全合成：具有连续四元立体中心的多功能异丁烷环系统的简便组装
4. I. Studies on the organocatalytic formation of quaternary stereocenters. ii. Studies on the claisen rearrangement as a route to quaternary stereocenters. iii. Asymmetric synthesis of aldehydes bearing quaternary carbon centers via the decarboxylative asymmetric allylic alkylation. [D] . Alberch, Eduardo. 2013

机译：I.季铵立体中心的有机催化形成研究。 ii。关于克莱森重排作为四元立体中心路径的研究。 iii。通过脱羧不对称烯丙基烷基化反应不对称合成带有季碳中心的醛。
5. Diastereodivergent combined carbometalation/zinc homologation/C–C fragmentation reaction as an efficient tool to prepare acyclic allylic quaternary carbon stereocenters [O] . Sudipta Raha Roy, Dorian Didier, Amir Kleiner, 2016

机译：非对映结合碳金属化/锌同源化/ CC裂解反应作为制备无环烯丙基季碳立体中心的有效工具
6. Organocatalytic Sequential One-Pot Double Cascade Asymmetric Synthesis of Wieland-Miescher Ketone Analogues from a Knoevenagel/Hydrogenation/Robinson Annulation Sequence: Scope and Applications of Organocatalytic Biomimetic Reductions [O] . -1

机译：有机催化顺序单盆双级级级级联非对称合成Wielangagel /氢化/罗宾逊环导序列的威尔兰 - 米塞酮类似物：有机催化仿生减少的范围和应用

Expedient and Diastereodivergent Assembly of Terpenoid Decalin Subunits having Quaternary Stereocenters through Organocatalytic Robinson Annulation of Nazarov Reagent

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