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首页> 外文期刊>Chemistry: A European journal >A stereodivergent strategy for the preparation of corynantheine and ipecac alkaloids, their epimers, and analogues: Efficient total synthesis of (-)-dihydrocorynantheol, (-)-corynantheol, (-)-protoemetinol, (-)-corynantheal, (-)-protoemetine, and related natural and nonnatural compounds
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A stereodivergent strategy for the preparation of corynantheine and ipecac alkaloids, their epimers, and analogues: Efficient total synthesis of (-)-dihydrocorynantheol, (-)-corynantheol, (-)-protoemetinol, (-)-corynantheal, (-)-protoemetine, and related natural and nonnatural compounds

机译：制备胭脂红碱和吐根碱生物碱，它们的差向异构体和类似物的立体发散策略：（-）-二氢胭脂红酚，（-）-胭脂红酚，（-）-原型泛醇，（-）-胭脂红，（-）-普罗美汀，及相关的天然和非天然化合物

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摘要

Here we present a general and common catalytic asymmetric strategy for the total and formal synthesis of a broad number of optically active natural products from the corynantheine and ipecac alkaloid families, for example, indolo[2,3-a]- and benzo[a]quinolizidines. Construction of the core alkaloid skeletons with the correct absolute and relative stereochemistry relies on an enantioselective and diastereodivergent one-pot cascade sequence followed by an additional diastereodivergent reaction step. This allows for enantio- and diastereoselective synthesis of three out of four possible epimers of the quinolizidine alkaloids that begin from common and easily accessible starting materials by using a common synthetic route. Focus has been made on excluding protecting groups and limiting isolation and purification of synthetic intermediates. This methodology is applied in the total synthesis of the natural products (-)-dihydrocorynantheol, (-)-hirsutinol, (-)-corynantheol, (-)-protometinol, (-)-dihydrocorynantheal, (-)-corynantheal, (-)-protoemetine, (-)-(15S)-hydroxydihydrocorynantheol, and an array of their nonnatural epimers. The potential of this strategy is also demonstrated in the synthesis of biologically interesting natural product analogues not accessible through synthetic elaboration of alkaloid precursors available from nature, for example, thieno[3,2-a]quinolizidine derivatives. We also report the formal synthesis of (+)-dihydrocorynantheine, (-)-emetine, (-)-cephaeline, (-)-tubulosine, and (-)-deoxytubulosine.
机译：在这里，我们提出了一种通用和通用的催化不对称策略，用于从大红霉素和吐根碱生物碱家族，例如吲哚[2,3-a]-和苯并[a]的多种光学活性天然产物的全部和形式合成。喹唑烷类。具有正确的绝对和相对立体化学的核心生物碱骨架的构建依赖于对映选择性和非对映异构的一锅级联序列，然后进行附加的非对映异构反应步骤。这允许对喹诺酮生物碱的四种可能的差向异构体中的三种进行对映异构和非对映选择性合成，这些异构体是通过使用常见的合成途径从常见且易于获得的起始原料开始的。已经集中在排除保护基和限制合成中间体的分离和纯化上。该方法学应用于天然产物（-）-二氢甲氧萘丁酚，（-）-hirsutinol，（-）-甲氧丁苯酚，（-）-异丙甲酚，（-）-二氢甲氧丁苯酚，（-）-甲氧乙醛，（- ）-protoemetine，（-）-（15S）-羟基二氢六氢萘酚及其一系列非天然差向异构体。这种策略的潜力在合成生物学上令人关注的天然产物类似物时也得到了证明，这些合成物不能通过合成加工得自自然界的生物碱前体（例如，噻吩并[3,2-a]喹喔啉衍生物）来获得。我们还报告了（+）-dihydrocorynantheine，（-）-metetine，（-）-cephaeline，（-）-tubulosine和（-）-deoxytubulosine的正式合成。

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