含托酚酮倍半萜类化合物奥拉西姆苷A及其脱羰类似物奥拉西姆苷B的全合成
Total Syntheses of the Tropolone-Containing Sesquiterpene Olaximbriside A and Its Decarbonylated Counterpart Olaximbriside B.
作者信息
Chen Qi, Banwell Martin G, Gardiner Michael G, Lan Ping, Tan Shen
机构信息
Institute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan University, Guangzhou 510632, China.
State Key Laboratory of Bioactive Molecules and Druggability Assessment, Jinan University, Guangzhou 510632, China.
出版信息
J Org Chem. 2024 Sep 20;89(18):13530-13539. doi: 10.1021/acs.joc.4c01738. Epub 2024 Sep 12.
The racemic modification of the α-tropolone-containing sesquiterpene olaximbriside A [viz. (±)-)] has been prepared over 12 steps from the readily accessible decalin derivative . The last two of these steps involve a fully regiocontrolled substitution reaction of bromotropone . The aromatization of a stereoisomeric and co-produced form of compound has provided (±)-olaximbriside B [(±)-)].
含α-托酚酮的倍半萜olaximbriside A的外消旋体[即(±)-]已从易于获得的十氢化萘衍生物经12步反应制备得到。其中最后两步涉及溴托酚酮的完全区域选择性取代反应。化合物的一种立体异构体和共生产物形式的芳构化反应得到了(±)-olaximbriside B[(±)-]。
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