Department of Chemistry , University of Pretoria , Lynnwood Road , Hatfield , Pretoria 0002 , South Africa.
Radiochemistry , South African Nuclear Energy Corporation (Necsa) , Pelindaba , Brits 0240 , South Africa.
J Nat Prod. 2019 Nov 22;82(11):3074-3082. doi: 10.1021/acs.jnatprod.9b00681. Epub 2019 Nov 8.
The unexpected conversion of benzoylbenzofurans into isoflavones through an intramolecular cascade that involves deprotection and ring-opening/cyclization is described. This was discovered in an investigation of the possible transformation of benzoylbenzofurans into coumaronochromones. This route affords isoflavones in two major steps from acetophenones and benzoquinones. The transformation was validated by synthesizing differently substituted isoflavone derivatives and further applied to a concise synthesis of a potential anticancer lead compound, glaziovianin A ().
本文描述了通过涉及去保护和开环/环化的分子内级联反应，将苯甲酰苯并呋喃意外转化为异黄酮的过程。这一发现源于对苯甲酰苯并呋喃可能转化为香豆素酮的研究。该路线通过两步反应，从苯乙酮和苯醌出发，以较高的收率得到异黄酮。该转化通过合成不同取代的异黄酮衍生物得到验证，并进一步应用于潜在抗癌先导化合物 glaziovianin A（）的简洁合成。
