A new, iterative strategy for the synthesis of unsymmetrical polyynes: application to the total synthesis of 15,16-dihydrominquartynoic acid.
[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.
Kim
Sanghee
S
College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea. pennkim@snu.ac.kr
Kim
Shinae
S
Lee
Taeho
T
Ko
Hyojin
H
Kim
Deukjoon
D
D000480:Alkynes / Q000138:chemical synthesis*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D015394:Molecular Structure; D053279:Polyynes
D000480:Alkynes; D005231:Fatty Acids, Unsaturated; D007202:Indicators and Reagents; C417933:minquartynoic acid; D053279:Polyynes