A concise total synthesis of arizonins B1 and C1 |
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Authors: | Rodney A Fernandes Sandip V Mulay Vijay P Chavan |
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Institution: | Department of Chemistry, Indian Institute of Technology Bombay, Powai 400076, Mumbai, Maharashtra, India |
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Abstract: | A concise and efficient total synthesis of arizonins B1 and C1 is reported. A key building block alkyne is synthesized from d-glucono-δ-lactone and used in the Dötz benzannulation reaction to construct the naphthalene unit. An oxa-Pictet–Spengler reaction gave the pyran ring while an H2SO4 mediated isomerization set the correct stereochemistry of the target molecules. Alternatively, a direct anti-pyran stereochemistry was prepared in a TFA solvent. The synthesis is competitive to previous reports and marks the first enantioselective synthesis of arizonin B1. |
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