The first example of Nazarov reactions of vinyl cumulenyl ketones.
[reaction: see text] alpha-Lithio cumulenyl ethers can be prepared in situ and converted to alpha-allenyl cyclopentenones. Isomerization of the product of one such reaction has led to a furanyl cyclopentenone, the core structure of nakadomarin A.
Leclerc
Eric
E
Department of Chemistry, University of Hawaii, and The Cancer Research Center of Hawaii, Honolulu, Hawaii USA.
Tius
Marcus A
MA
D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D004987:Ethers / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D007659:Ketones / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
D003517:Cyclopentanes; D004987:Ethers; D005663:Furans; D007659:Ketones; D014753:Vinyl Compounds; C013905:cyclopentenone