Pyrrolizidines, indolizidines and quinolizidines via a double reductive cyclisation protocol: concise asymmetric syntheses of (+)-trachelanthamidine, (+)-tashiromine and (+)-epilupinine

Brambilla Marta; Davies Stephen G.; Fletcher Ai M.; Roberts Paul M.; Thomson James E.; Zimmer David

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Pyrrolizidines, indolizidines and quinolizidines via a double reductive cyclisation protocol: concise asymmetric syntheses of (+)-trachelanthamidine, (+)-tashiromine and (+)-epilupinine

机译：通过双重还原环化方案的吡咯并立核苷，吲哚并立核苷和喹啉并立核苷：（+）-四氢鸟啶，（+）-ta郎胺和（+）-埃拉品丙胺的简明不对称合成

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The asymmetric syntheses of pyrrolizidine, indolizidine and quinolizidine alkaloids have been achieved using the diastereoselective conjugate addition of lithium (R)-N-benzyl-N-(alpha-methylbenzyl)amide to alpha-alkenyl-alpha,beta-unsaturated esters followed by diastereoselective protonation of the resultant enolates as the key stereodefining steps. The azabicyclic scaffolds were then efficiently constructed upon sequential oxidative cleavage of the olefinic units within the resultant beta-amino esters and hydrogenolytic N-de-benzylation of the corresponding dialdehydes, which occurs with concomitant double reductive cyclisation. Subsequent reduction of the ester moieties with LiAIH(4) gave (+)-trachelanthamidine, (+)-tashiromine, (1S,8aR)-1-(hydroxymethyl)octahydroindolizine and (+)-epilupinine in 4.9, 4.1, 3.0 and 5.9% overall yield, respectively, in only six steps from commercially available starting materials. (C) 2016 Elsevier Ltd. All rights reserved.

机译：使用锂（R）-N-苄基-N-（α-甲基苄基）酰胺的非对映选择性共轭加成至α-烯基-α，β-不饱和酯，然后进行非对映选择性，已实现了吡咯烷核苷，吲哚并立氮唑和喹喔啉生物碱的不对称合成合成的质子化成为关键的立体定义步骤。然后在所得的β-氨基酯中的烯烃单元的顺序氧化裂解和相应的二醛的氢解N-脱苄基作用之后，有效地构建氮杂双环支架，其伴随双重还原环化而发生。随后用LiAIH（4）还原酯部分，得到4.9、4.1、3.0和5.9中的（+）-四氢ham啶，（+）-tashiromine，（1S，8aR）-1-（羟甲基）八氢吲哚嗪和（+）-癫痫碱从市售起始原料仅在六个步骤中分别获得总收率的％。（C）2016 Elsevier Ltd.保留所有权利。

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《Tetrahedron》 |2016年第47期|共13页
作者
Brambilla Marta; Davies Stephen G.; Fletcher Ai M.; Roberts Paul M.; Thomson James E.; Zimmer David;
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(+)-Trachelanthamidine; (+)-Tashiromine; (+)-Epilupinine; Azabicyclic alkaloids; Asymmetric synthesis;

机译：（+）-Trachelanthamidine;（+）-Tashiromine;（+）-Epilupinine;氮杂双环生物碱;不对称合成;

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1. Pyrrolizidines, indolizidines and quinolizidines via a double reductive cyclisation protocol: concise asymmetric syntheses of (+)-trachelanthamidine, (+)-tashiromine and (+)-epilupinine [J] . Brambilla Marta, Davies Stephen G., Fletcher Ai M., Tetrahedron . 2016,第47期

机译：通过双重还原环化方案的吡咯并立核苷，吲哚并立核苷和喹啉并立核苷：（+）-四氢鸟啶，（+）-ta郎胺和（+）-埃拉品丙胺的简明不对称合成
2. Organocatalytic Asymmetric Mannich Cyclization of Hydroxylactams with Acetals: Total Syntheses of (-)-Epilupinine, (-)-Tashiromine, and (-)-Trachelanthamidine [J] . Koley Dipankar, Krishna Yarkali, Srinivas Kyatham, Angewandte Chemie . 2014,第48期

机译：乙缩醛与乙醛的有机催化不对称曼尼希环化：（-）-艾拉匹宁，（-）-Tashiromine和（-）-Trachelanthamidine的总合成
3. A common approach to pyrrolizidine and indolizidine alkaloids; Formal synthesis of (-)-isoretronecanol, (-)-trachelanthamidine and an approach to the synthesis of (-)-5-epitashiromine and (-)-tashiromine [J] . Reddy K.K.S., Rao B.V., Raju S.S. Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2011,第6期

机译：吡咯嗪和吲哚并立生物碱的常用方法; （-）-异戊烯醇，（-）-四氢邻苯二甲胺的正式合成以及（-）-5-表异四胺和（-）-四ta碱的合成方法
4. An RCM strategy for the enantiosynthesis of new polyhydroxylated quinolizidines, indolizidines and pyrrolizidines(Abstracts) [C] . Alessandro Sacchetti, Giordano Lesma, Alessia Colombo European Symposium on Organic Chemistry . 2007

机译：新型多羟基化喹硫吡啶，吲哚状物和吡咯醇（摘要）对映映的RCM策略（摘要）
5. New phosphine-diamine and phosphine-amino-alcohol tridentate ligands for ruthenium catalysed enantioselective hydrogenation of ketones and a concise lactone synthesis enabled by asymmetric reduction of cyano-ketones [O] . José A Fuentes, Scott D Phillips, Matthew L Clarke 2012

机译：用于钌催化酮的对映选择性氢化的新膦二胺和膦氨基氨基醇三齿配体以及通过不对称还原氰基酮实现的简洁内酯合成
6. Asymmetric Synthesis of Pyrrolizidines, Indolizidines and Quinolizidines via a Double Reductive Cyclisation Protocol [O] . Stephen Davies, Ai Fletcher, Paul Roberts, 2017

机译：通过双还原环化方案不对称合成吡咯里西嗪，吲嗪嗪和喹嗪类

Pyrrolizidines, indolizidines and quinolizidines via a double reductive cyclisation protocol: concise asymmetric syntheses of (+)-trachelanthamidine, (+)-tashiromine and (+)-epilupinine

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