1,3,4-噁二唑的跨环 Diels-Alder/1,3-偶极环加成级联反应：独特长春碱类似物的全合成。
Transannular Diels-Alder/1,3-dipolar cycloaddition cascade of 1,3,4-oxadiazoles: total synthesis of a unique set of vinblastine analogues.
机构信息
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
出版信息
Org Lett. 2013 Oct 18;15(20):5306-9. doi: 10.1021/ol402549n. Epub 2013 Oct 2.
Abstract
A powerful tandem [4 + 2]/[3 + 2] cycloaddition cascade of 1,3,4-oxadiazoles initiated by a transannular [4 + 2] cycloaddition is detailed. An impressive four rings, four carbon-carbon bonds, and six stereocenters are set on each site of the newly formed central six-membered ring in a cascade thermal reaction that proceeds at temperatures as low as 80 °C. The resulting cycloadducts provide the basis for the synthesis of unique analogues of vinblastine containing metabolically benign deep-seated cyclic modifications at the C3/C4 centers of the vindoline-derived subunit of the natural product.
摘要
详细介绍了由环加成引发的 1,3,4-恶二唑的强串联[4 + 2]/[3 + 2]环加成级联反应。在温度低至 80°C 的级联热反应中，每个新形成的中环的六个位置上都设置了令人印象深刻的四个环、四个碳-碳键和六个立体中心。所得的环加成产物为合成含有代谢良性深层环状修饰的独特长春碱类似物提供了基础，这些修饰位于天然产物的长春花衍生亚基的 C3/C4 中心。
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