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Title: Intramolecular direct dehydrohalide coupling promoted by KO(t)Bu: total synthesis of Amaryllidaceae alkaloids anhydrolycorinone and oxoassoanine. Author: De S, Ghosh S, Bhunia S, Sheikh JA, Bisai A. Journal: Org Lett; 2012 Sep 07; 14(17):4466-9. PubMed ID: 22892050. Abstract: A transition-metal-free intramolecular dehydrohalide coupling via intramolecular homolytic aromatic substitution (HAS) with aryl radicals has been developed in the presence of potassium tert-butoxide and an organic molecule as the catalyst. The methodology has been applied to a concise synthesis of Amaryllidaceae alkaloids viz. oxoassoanine (1b), anhydrolycorinone (1d), and other related structures. Interestingly, the method also works only in the presence of potassium tert-butoxide.[Abstract] [Full Text] [Related] [New Search]