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Asymmetric total synthesis of (+)-isocryptotanshinone and formal synthesis of (−)-cryptotanshinone
Institution:1. Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro, NM 87801, USA;2. Department of Biology, New Mexico Institute of Mining and Technology, Socorro, NM 87801, USA;3. Center for Integrated Protein Science at the Department Chemie, Technische Universitat München, Lichtenbergstraße 4, 85748 Garching, Germany;1. Nano Science and Technology Institute, University of Science and Technology of China, Suzhou 215123, China;2. ShanghaiTech University, Shanghai 20120, China;3. CAS Key Laboratory of Receptor Research, Synthetic Organic & Medicinal Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China;4. University of Chinese Academy of Sciences, Beijing 100049, China;1. Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri, Bhopal - 462 066, Madhya Pradesh, India;2. Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, Nadia - 741 246, West Bengal, India;1. California State University Fullerton, Department of Chemistry and Biochemistry, Fullerton, CA 92831, USA;2. Department of Chemistry and Biochemistry, San Francisco State University, San Francisco, CA 94132, USA
Abstract:The first asymmetric total synthesis of (+)-isocryptotanshinone was achieved in 12 linear steps with 12% overall yield from commercially available dihydrobenzopyrone. The key step was a base-mediated cyclization reaction. In addition, the synthetic strategy included the formal synthesis of (−)-cryptotanshinone.
Keywords:(+)-isocryptotanshinone  Asymmetric total synthesis  (−)-Cryptotanshinone  STAT3 inhibitor  Base-mediated cyclization
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