Recent Natural Product Total Syntheses Involving Cycloadditions of Allenes

IF 5.5 1区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY
Chen-Chen Gu, Xiong-En Long, Xiuping Chen, Junyang Liu, Chuang-Chuang Li
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Abstract

Comprehensive Summary

Allenes, characterized by their cumulated carbon–carbon double bonds, have emerged as indispensable synthons in the construction of complex natural products. Their unique reactivity and stereochemical properties render allenes a powerful tool for the efficient and streamlined total synthesis of structurally intricate natural products. This review comprehensively summarizes the total syntheses of complex natural products involving allene cycloaddition reactions reported over the past decade (2014—2024). Among the nearly 20 total syntheses reviewed, the [2+1], [2+2], [3+2], [4+2], [4+3], [5+1] and [2+2+1] cycloaddition reactions of allenes are the most important transformations to construct the key skeleton. This is because of their ability to form multiple bonds in a single step with high atom economy, stereoselectivity, and regioselectivity, often under mild conditions. The strategic application of these reactions in forming key carbon–carbon bonds and controlling stereochemistry makes them practical for the efficient assembly of complex molecular frameworks. With the ongoing exploration of methods for allene generation, particularly the enantioselective approaches, and the continued discovery of novel cyclization reactions of allenes, allene chemistry will maintain its crucial and indispensable role in the total synthesis of natural products.

Key Scientists

含环加成烯的天然产物全合成新进展
烯类化合物由于其碳碳双键的累积而成为构建复杂天然产物不可缺少的合成物。其独特的反应活性和立体化学性质使烯类化合物成为结构复杂的天然产物高效、流线型全合成的有力工具。本文综述了近十年(2014-2024)报道的涉及烯环加成反应的复杂天然产物的全合成。在综述的近20种全合成中,烯的[2+1]、[2+2]、[3+2]、[4+2]、[4+3]、[5+1]和[2+2+1]环加成反应是构建关键骨架最重要的转化。这是因为它们能够在一个步骤中形成多个键,具有高原子经济性,立体选择性和区域选择性,通常在温和的条件下。这些反应在形成关键碳-碳键和控制立体化学中的策略性应用,使它们成为复杂分子框架的有效组装。随着对烯生成方法的不断探索,特别是对映选择方法的不断探索,以及对烯的新型环化反应的不断发现,烯化学将在天然产物的全合成中保持其至关重要和不可或缺的作用。关键的科学家
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来源期刊
Chinese Journal of Chemistry
Chinese Journal of Chemistry 化学-化学综合
CiteScore
8.80
自引率
14.80%
发文量
422
审稿时长
1.7 months
期刊介绍: The Chinese Journal of Chemistry is an international forum for peer-reviewed original research results in all fields of chemistry. Founded in 1983 under the name Acta Chimica Sinica English Edition and renamed in 1990 as Chinese Journal of Chemistry, the journal publishes a stimulating mixture of Accounts, Full Papers, Notes and Communications in English.
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