7734. Prelog-Djerassi Lactone
Nomenclature
CAS number: 69056-12-8
(αR,2S,3S,5R)-Tetrahydro-α,3,5-trimethyl-6-oxo-2H-pyran-2-acetic acid; (+)-Prelog-Djerassi lactonic acid; 6-(1-carboxyethyl)-3,4,5,6-tetrahydro-3,5-dimethyl-2-pyranone. C10H16O4; mol wt 200.23.
C 59.98%, H 8.05%, O 31.96%.
Description and references
Intermediate in the synthesis of macrolide antibiotics. Isoln as degradation product of narbomycin, q.v.: R. Anliker et al., Helv. Chim. Acta 39, 1785 (1956); of methymycin, q.v.: C. Djerassi, J. A. Zderic, J. Am. Chem. Soc. 78, 6390 (1956). Abs config: R. W. Rickards, R. M. Smith, Tetrahedron Lett. 1970, 1025. Synthesis: P. A. Grieco et al., J. Am. Chem. Soc. 101, 4749 (1979); D. A. Evans, J. Bartroli, Tetrahedron Lett. 23, 807 (1982). Synthesis of (±)-form: S. Masamune et al., J. Am. Chem. Soc. 97, 3512 (1975); C. Santelli-Rouvier et al., Tetrahedron Lett. 35, 6101 (1994). Review of stereoselective syntheses: S. F. Martin, D. E. Guinn, Synthesis 1991, 245.
