Total synthesis of (+)-madindoline A and (+)- madindoline B
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2006
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University of Hawaii at Manoa
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A formal total synthesis of (+ )-madindoline A and (+ )-madindoline B, highly selective inhibitors of interleukin-6, has been accomplished in 11 steps with an overall yield of 8.3% from hexanoic acid. The allene ether version of the Nazarov cyc1ization was used to form the cyclopentenone core of the madindolines. The quaternary carbon center was generated from a ZnBr2-catalyzed condensation reaction between silyl enol ether 2.24 and thioether 2.50.
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Indole, Cells--Growth--Regulation
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Theses for the degree of Master of Science (University of Hawaii at Manoa). Chemistry; no. 4148
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