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丁基-2-苄氧基苯甲酰胺的维蒂希重排反应在邻苯二甲酸内酯天然产物及3-芳基-3-苄氧基异吲哚啉酮类抗癌药物合成中的应用

Application of the Wittig Rearrangement of -Butyl-2-benzyloxybenzamides to Synthesis of Phthalide Natural Products and 3-Aryl-3-benzyloxyisoindolinone Anticancer Agents.

作者信息

Aitken R Alan, Cooper Francesca K, Harper Andrew D, Inwood Ryan A, Saab Elizabeth A, Soutar Ewan J

机构信息

EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St. Andrews KY16 9ST, Fife, UK.

出版信息

Molecules. 2024 Oct 6;29(19):4722. doi: 10.3390/molecules29194722.

DOI:10.3390/molecules29194722
PMID:39407650
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11478121/
Abstract

Application of the [1,2]-Wittig rearrangement and cyclisation approach to 3-arylphthalides has been evaluated for the synthesis of three bioactive natural products. While this is successful in the case of crycolide, providing the second synthesis of this compound, the more sterically demanding targets isopestacin and cryphonectric acid prove not to be amenable to this approach, with the 2,6-disubstituted aryl groups causing the failure of the rearrangement and alkylation steps, respectively. Direct oxidation of the substituted benzhydrols resulting from [1,2]-Wittig rearrangement using MnO provides a new route to 3-aryl-3-hydroxyisoindolinones, and this method has been used in the synthesis of two 3-aryl-3-benzyloxyisoindolinone anticancer agents.

摘要

已评估将[1,2]-维蒂希重排和环化方法应用于3-芳基苯酞类化合物用于合成三种生物活性天然产物的情况。虽然在crycolide的合成中这一方法取得了成功，实现了该化合物的第二次合成，但空间位阻要求更高的目标产物异黄绿青霉素和隐杯伞素酸并不适合这种方法，2,6-二取代芳基分别导致重排步骤和烷基化步骤失败。使用MnO对[1,2]-维蒂希重排产生的取代二苯甲醇进行直接氧化，为3-芳基-3-羟基异吲哚啉酮提供了一条新路线，该方法已用于合成两种3-芳基-3-苄氧基异吲哚啉酮抗癌剂。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53a5/11478121/5af7d8f5e23a/molecules-29-04722-g003.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53a5/11478121/129b2e669885/molecules-29-04722-sch002.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53a5/11478121/6356fab765ee/molecules-29-04722-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53a5/11478121/2ac0adf7e3bb/molecules-29-04722-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53a5/11478121/36ce5cc62b7e/molecules-29-04722-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53a5/11478121/f3281b9dfd78/molecules-29-04722-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53a5/11478121/5ded9dd327d7/molecules-29-04722-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53a5/11478121/5af7d8f5e23a/molecules-29-04722-g003.jpg

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