Recent Advances for the Synthesis of α-Alkylidene-γ-lactones

doi:10.6023/cjoc202601016

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (4): 1205-1221.DOI: 10.6023/cjoc202601016 Previous Articles Next Articles

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α-烯基-γ-内酯的合成进展

韩昕冉^a^,^†, 霍恒宇^a^,^†, 宋学攀^b, 舒超^a^,^*()

^a 华中师范大学化学学院光能利用与减污降碳教育部工程研究中心绿色农药全国重点实验室武汉 430079
^b 中国标准药物集团有限公司湖北黄石 435002

收稿日期:2026-01-13 修回日期:2026-03-10 发布日期:2026-04-13
通讯作者: 舒超
作者简介:
^† 共同第一作者
基金资助:
国家自然科学基金(22571109); 国家自然科学基金(22301093)

Recent Advances for the Synthesis of α-Alkylidene-γ-lactones

Xinran Han^a, Hengyu Huo^a, Xuepan Song^b, Chao Shu^a^,^*()

^a State Key Laboratory of Green Pesticide, Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, College of Chemistry, Central China Normal University, Wuhan 430079
^b China National Standard Pharmaceutical Co., Ltd., Huangshi, Hubei 435002

Received:2026-01-13 Revised:2026-03-10 Published:2026-04-13
Contact: Chao Shu
About author:
^†These authors contributed equally to this work
Supported by:
National Natural Science Foundation of China(22571109); National Natural Science Foundation of China(22301093)

α-Alkylidene-γ-lactone skeletons, which possess multiple biological properties, are core structural motifs found in numerous natural products and active pharmaceuticals. Over the past several years, signiﬁcant progress has been made in the development of efﬁcient and selective catalytic methods for the synthesis of α-alkylidene-γ-lactones under relatively mild conditions with new synthetic technologies. However, a comprehensive summary of this field has yet to be established in the literature of the past decade. The typical α-alkylidene-γ-lactone-containing natural and unnatural bioactive molecules, as well as highlights the recent advancements in the preparation of α-alkylidene-γ-lactone derivatives are introduced. It is hoped that this overview will inspire the development of novel strategies for accessing diverse α-alkylidene-γ-lactones and facilitate their applications in drug discovery.

Key words: α-alkylidene-γ-lactone, natural product, synthesis, radical-polar crossover cyclization, bioactivity

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Xinran Han, Hengyu Huo, Xuepan Song, Chao Shu. Recent Advances for the Synthesis of α-Alkylidene-γ-lactones[J]. Chinese Journal of Organic Chemistry, 2026, 46(4): 1205-1221.

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Fig. & Tab. 26

Figure 1. Representative bioactive molecules and drug candidates containing α-alkylidene-γ-butyrolactones

Figure 2. Sesquiterpenes containing α-alkylidene-γ-lactone unit

Figure 3. Germacranolides containing α-alkylidene-γ-lactone unit

Figure 4. Guaianolides containing α-alkylidene-γ-lactone unit

Figure 5. Examples of pseudoguaianolides containing α-alkyli- dene-γ-lactone unit

Figure 6. Examples of eudesmanolides containing α-alkylidene- γ-lactone unit

Figure 7. Examples of xanthanolides containing α-alkylidene- γ-lactone unit

Figure 8. Example of carabrone containing α-alkylidene- γ-lactone unit

Figure 9. Examples of diterpenoids containing α-alkylidene- γ-lactone unit

Figure 10. Examples of non-terpenoids containing α-alkylidene- γ-lactone unit

Scheme 1. Intramolecular Rauhut-Currier reaction to chiral α-alkylidene-γ-butyrolactones

Scheme 2. An enantioselective intramolecular Rauhut-Currier reaction to the synthesis of α-alkylidene-γ-butyrolactones

Scheme 3. Catalytic enantioselective amide allylation of isatins to α-methylene-γ-butyrolactones containing 2-oxindole derivatives

Scheme 4. Indium-mediated Barbier-type reaction and selective reduction of the exocyclic double bond to α-methylene-γ-butyrolactones containing 2-oxindole derivatives

Scheme 5. Tin powder-promoted one-pot synthesis of α-methylene-γ-butyrolactones containing 2-oxindole derivatives

Scheme 6. Rhodium-catalyzed one-pot C—H insertion/olefina- tion sequence to α-methylene-γ-lactone derivatives

Scheme 7. Rh2(OAc)4-catalyzed intramolecular C—H insertion of α-diazo α-phosphoryl cycloalkyl esters and subsequent alkylation/reductive alkylation or HWE reaction

Scheme 8. Bi(OTf)3-catalyzed, dehydrative, ring-opening cyclizations of cyclopropyl carbinols to α-methylene-γ-butyrolactone derivatives

Scheme 9. Indium-mediated Barbier allyl addition to aldehydes

Scheme 10. Two synthetic routes of target α-methylene- γ-butyrolactone derivatives via lactonization according to the natural product carabrone discovered in a kind of plants

Scheme 11. Pd-catalyzed intermolecular asymmetric carboesterification of alkenes with alkynes to afford α-methylene γ-lactones

Scheme 12. Pd-catalyzed cascade carboesterification of alkynoic acids with alkenes in ionic liquids to α-methylene γ-lactones

Scheme 13. General synthetic method to generate α-arylidene diacylglycerol-lactones

Scheme 14. Iron-catalyzed reductive radical cascade reaction of allyl alcohols and acetylenic acids to α-alkenyl lactones via reflex- Michael addition

Scheme 15. Visible-light-induced radical-polar crossover cyclization reaction to synthesize α-exo-alkenyl γ-lactones

Scheme 16. Palladium-catalyzed cascade reaction for the synthesis of diverse heterocycle-containing γ-alkylidenebutenolides

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α-烯基-γ-内酯的合成进展

Recent Advances for the Synthesis of α-Alkylidene-γ-lactones

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