Metal-catalyzed coupling reactions on an olefin template: the total synthesis of (13E,15E,18Z,20Z)-1-hydroxypentacosa- 13,15,18,20-tetraen-11-yn-4-one 1-acetate.
The naturally occurring ant venom (13E,15E,18Z,20Z)-1-hydroxypentacosa-13,15,18,20-tetraen-11-yn-4-one 1-acetate was synthesized stereospecifically using a series of metal-mediated cross-coupling reactions. The use of the difunctional olefin template (E)-1-chloro-2-iodoethylene as the central, pseudosymmetrical building block facilitated a fully convergent and, thus, efficient strategy to prepare this polyunsaturated natural product.
Organ
Michael G
MG
The Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, Canada M3J 1P3. organ@yarku.ca
Ghasemi
Haleh
H
D000085:Acetates / Q000138:chemical synthesis*; D000480:Alkynes / Q000138:chemical synthesis*; D000862:Ant Venoms / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D005030:Ethylenes / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D010984:Platinum / Q000737:chemistry*; D013237:Stereoisomerism
C485018:(13E,15E,18Z,20Z)-1-hydroxypentacosa-13,15,18,20-tetraen-11-yn-4-one 1-acetate; D000085:Acetates; D000480:Alkynes; D000862:Ant Venoms; D005030:Ethylenes; D006843:Hydrocarbons, Chlorinated; D006847:Hydrocarbons, Iodinated; D010984:Platinum