Catalytic Asymmetric Synthesis of Benzobicyclo [3.2. 1] octanes

M Anif Pasha, S Peraka… - Chemistry–A European …, 2021 - Wiley Online Library
Chemistry–A European Journal, 2021Wiley Online Library
Lawsone aldehydes were directly transformed into the biologically important, unique carbon
skeleton of chiral methanobenzo [f] azulenes/methanodibenzo [a, d][7] annulenes in high dr
and ee and in very good yields by using quinine‐thiourea‐catalyzed tandem
Wittig/intramolecular Michael/intramolecular aldol reactions. This asymmetric catalytic
tandem protocol will be highly useful because these final molecules are basic skeletons of
important antibiotics.
Abstract
Lawsone aldehydes were directly transformed into the biologically important, unique carbon skeleton of chiral methanobenzo[f]azulenes/methanodibenzo[a,d][7]annulenes in high dr and ee and in very good yields by using quinine‐thiourea‐catalyzed tandem Wittig/intramolecular Michael/intramolecular aldol reactions. This asymmetric catalytic tandem protocol will be highly useful because these final molecules are basic skeletons of important antibiotics.
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