A new, iterative strategy for the synthesis of unsymmetrical polyynes: application to the total synthesis of 15,16-dihydrominquartynoic acid |
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Authors: | Kim Sanghee Kim Shinae Lee Taeho Ko Hyojin Kim Deukjoon |
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Affiliation: | College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea. pennkim@snu.ac.kr |
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Abstract: | [reaction: see text] A new iterative strategy for the synthesis of unsymmetrically substituted polyynes has been developed. The starting bromoalkyne is homologated by one acetylene unit through palladium-catalyzed cross-coupling with a TIPS-protected terminal acetylene and a subsequent in situ one-pot AgF-mediated desilylative bromination. The utility of this new synthetic method is demonstrated by its application to the total synthesis of (S)-(E)-15,16-dihydrominquartynoic acid. |
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