Enantioselective synthesis of the C1-C6 and C7-C23 fragments of the proposed structure of iriomoteolide 1a |
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| Authors: | Crimmins Michael T Dechert Anne-Marie R |
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| Institution: | Kenan, Caudill, Venable and Murray Laboratories of Chemistry, University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599, United States. crimmins@email.unc.edu |
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| Abstract: | Synthesis of the C1-C6 and C7-C23 fragments of the proposed structure of iriomoteolide 1a has been accomplished. Key steps include a cross metathesis to form the C15-C16 E olefin and a chelation controlled Grignard addition to form the tertiary alcohol at C14. Notably, 7 of the 9 stereocenters of the proposed structure have been set using various aldol reactions employing metallo enolates of thiazolidinethiones. |
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