期刊
TETRAHEDRON-ASYMMETRY
卷 24, 期 24, 页码 1548-1555出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2013.10.011
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资金
- Department of Science and Technology, New Delhi [SR/S1/OC-25/2008]
- Board of Research in Nuclear sciences (BRNS), Government of India [2009/37/25 BRNS]
- Council of Scientific and Industrial Research (CSIR) New Delhi
A concise and efficient total synthesis of arizonins B1 and C1 is reported. A key building block alkyne is synthesized from a-glucono-S-lactone and used in the Dotz 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. (C) 2013 Elsevier Ltd. All rights reserved.
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