Unified, radical-based approach for the synthesis of spiroketals.
[reaction: see text] Functionalization of S-(3-chloro-2-oxo-propyl)-O-ethyl xanthate 1 by two consecutive xanthate transfer reactions, followed by spirocyclization of the resulting dihydroxy ketones, provides a flexible and highly convergent access to diversely substituted spiroketals, containing five-, six-, and seven-membered rings.
de Greef
Michiel
M
Laboratoire de Synthèse Organique associé au C.N.R.S., Ecole Polytechnique, 91128 Palaiseau, France.
Zard
Samir Z
SZ
D001688:Biological Products / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D007982:Levulinic Acids / Q000737:chemistry; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry*
D001688:Biological Products; D005609:Free Radicals; D007982:Levulinic Acids; D013141:Spiro Compounds; C021959:2-amino-4-oxo-5-chloropentanoate