Formal synthesis of (±)-brazilin and total synthesis of (±)-brazilane |
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Authors: | Jhillu Singh Yadav Anand Kumar MishraSaibal Das |
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Institution: | Natural Products Chemistry Division, CSIR Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, AP, India |
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Abstract: | A convergent synthesis towards (±)-brazilin and (±)-brazilane has been reported from 3,4-dimethoxy benzaldehyde in <15 reaction steps. Palladium(II)-catalysed intramolecular Friedel–Crafts cyclisation and Lewis acid supported intermolecular Friedel–Crafts alkylation reactions have been demonstrated. A tetracyclic substituted indane common key intermediate is employed to furnish the desired two molecules in good to excellent yield. Pd(OH)2 has played a crucial role in the total synthesis of (±)-brazilane. |
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Keywords: | Brazilin Brazilane Haematoxylin Brazilien Pearlmann reagent |
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