6191. Milbemycins
Nomenclature
Description and references
A family of novel macrolide antibiotics with insecticidal and acaricidal activity; structurally related to avermectin, q.v., aglycones. Isoln from Streptomyces hygroscopicus subsp. aureolacrimosus and properties: A. Aoki et al., DE 2329486; eidem, US 3950360 (1973, 1976 both to Sankyo); of α1-α10, β1-β3, D-H: Y. Takiguchi et al., J. Antibiot. 33, 1120 (1980). Isoln and properties of D-H: Y. Takiguchi et al., J. Antibiot. 36, 502 (1983); of J and K: M. Ono et al., ibid. 509. Structures of milbemycins α1-α10, β1: M. Kurabayashi et al., 18th Symp. Chem. Natural Products (Kyoto, 1974) nos. 309-316; of β1-β3: H. Mishima et al., Tetrahedron Lett. 1975, 711; of D-H, J, K: H. Mishima et al., J. Antibiot. 36, 980 (1983). Total synthesis of (±)-milbemycin β3: A. B. Smith et al., J. Am. Chem. Soc. 104, 4015 (1982); of the (+)-form: D. R. Williams et al., ibid. 4708. Prepn of milbemycins from avermectins: H. Mrozik et al., Tetrahedron Lett. 1983, 5333. Total synthesis studies of D: M. T. Crimmins et al., ibid. 28, 3651 (1987). Prophylactic use of milbemycin D against Dirofilaria immitis infection in dogs: M. Tagawa et al., Jpn. J. Vet. Sci. 47, 787 (1985). Toxicity data: N. Matsunuma et al., Sankyo Kenkyusho Nempo 35, 71 (1983), C.A. 101, 32870d (1984). Review of syntheses: T. Blizzard et al., in Recent Prog. Chem. Synth. Antibiotics, G. Lukacs, M. Ohno, Eds (Springer-Verlag, Berlin, 1990) pp 66-102. Review of structure-activity relationships: W. L. Shoop et al., Vet. Parasitol. 59, 139-156 (1995).
