Abstract: Herein, we report a mild and significant method for the synthesis of oxaspirocyclohexadienones by using a combination of Lewis acid-HFIP mediated [2+3]-annulation of p-quinone methides (p-QMs) and iodonium ylides. The proposed mechanism proceeds through a one-pot sequence of carbonyl activation/cyclopropyl formation/Cloke-Wilson rearrangement to provide a broad range of oxaspirocyclohexadienones in moderate to high yields. Interestingly, the spiro-annulated products were further converted to tetrahydroxanthane derivatives via BF3.OEt2 mediated dienone-phenol rearrangement pathway. Moreover, the spiro-annulated derivatives also showed a moderate anti-tuberculosis activity against Mycobacterium tuberculosis H37Ra ATCC25177.
Sanjeev Kumar is a journalist based in India, with a focus on national news. He has written for various publications, including MillenniumPost, BizzBuzzNews, Rediff.com India Ltd., and YourStory Media. His articles cover a wide range of topics, including politics, technology, aviation, and healthcare. Sanjeev's work has been featured in several renowned publications and media outlets in India and internationally.