Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 35, Pages 8014-8021Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201301126
Keywords
Total synthesis; Natural products; Medicinal chemistry; Biaryls; Oxidation
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Funding
- National Key Project for Basic Research [2010CB126100]
- National Natural Science Foundation of China (NSFC) [21132003, 21121002, 21002053]
- Tianjin Natural Science Foundation [11JCZDJC20500]
- National Key Technology Research and Development Program [2011BAE06B05]
- Specialized Research Fund for the Doctoral Program of Higher Education [20120031110010]
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A practical and scalable route was developed for the total synthesis of gossypol to allow for the construction of dozens of gossypol derivatives. tBuO(2)Ac was found to be a highly efficient oxidant for the polymerization of hemigossypol through a biosynthetic process under nonenzymatic conditions to give gossypol. Hemigossypol was synthesized on a gram scale by starting from commercially available carvacrol and dimethyl succinate and using a Stobbe condensation, an electrophilic cyclization, and the Michael addition of ortho-quinone methide as key steps.
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