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A concise total synthesis of arizonins B1 and C1

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
24
Issue
24
Identifiers
DOI: 10.1016/j.tetasy.2013.10.011
Disciplines
  • Chemistry

Abstract

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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