Intermolecular Radical Cation Diels-Alder (RCDA) Reaction of Bicyclooctadienes: Biomimetic Formal Total Synthesis of Kingianin A and Total Syntheses of Kingianins D, F, H, and J
Intermolecular Radical Cation Diels-Alder (RCDA) Reaction of Bicyclooctadienes: Biomimetic Formal Total Synthesis of Kingianin A and Total Syntheses of Kingianins D, F, H, and J
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DOI：
10.1021/jo402082y
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发表时间：
2014-02-07
影响因子：
3.6
通讯作者：
Parker, Kathlyn A.
中科院分区：
文献类型：
--
作者：
Lim, Hee Nam;Parker, Kathlyn A.
通过分子间自由基阳离子Diels-Alder（RCDA）反应，得到了三种内型双环辛二烯醇二聚体，分别对应于金姜素A和H、D、F和J。每种异构体在没有制备型HPLC的帮助下干净地分离。通过这些中间体，从市售原料分别经10步、13步、9步和17步制备了金姜素D、F、H和J。已经从这些化合物中的一种制备了金姜素A。完成金姜素H的合成依赖于Manchand的一步三碳同系化。
Three endo bicyclooctadienol dimers corresponding to kingianins A and H, D, and F and J were obtained by the intermolecular radical cation Diels-Alder (RCDA) reaction. Each isomer was cleanly isolated without the aid of preparative HPLC. kingianins D, F, H, and J were prepared by way of these intermediates from commercially available materials in 10, 13, 9, and 17 steps, respectively. Kingianin A has already been prepared from one of these compounds. Completion of the synthesis of kingianin H relied on Manchand's one-step, three-carbon homologation.