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A Concise Stereoselective Total Synthesis of Methoxyl Citreochlorols and Their Structural Revisions
European Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2021-02-19 , DOI: 10.1002/ejoc.202001563
Ranganayakulu Sunnapu 1 , Goreti Rajendar 1
Affiliation  

A concise, highly stereoselective and protecting group free total synthesis of methoxyl citreochlorols was demonstrated. All four stereoisomers were synthesized to establish the absolute stereochemistry of the reported structures and the structures were revised accordingly. An insitu generated silyl iodide promoted ring‐opening iodo esterification of lactones, a direct dichloromethylation of ester group and syn‐ & anti‐selective reduction of β‐hydroxy ketone were employed as key steps. The overall yields after eight‐step synthesis are obtained as 24 % and 21 % from commercially available (+) and (−)‐malic acids.
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中文翻译:

甲氧基Cytroochlorols的立体选择性全合成及其结构修订

证实了简明的,高度立体选择性的和无保护基的全合成甲氧基柠檬酰氯。合成了所有四种立体异构体,以建立所报道结构的绝对立体化学,并对结构进行了相应的修订。关键步骤包括原位生成的甲硅烷基碘化物促进内酯的碘代开环酯化,酯基的直接二氯甲基化以及β-羟基酮的顺式选择性还原。从市售的(+)和(-)-苹果酸中,八步合成后的总收率分别为24%和21%。
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更新日期:2021-03-16
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