6067. Methylenomycins
Description and references
Members of a family of cyclopentenoid antibiotics related structurally to sarkomycins, q.v., and having in vitro activity vs gram-positive and gram-negative organisms. Isoln from Streptomyces violaceoruber, physical, chemical, biological properties: M. Arai et al., JP Kokai 73 19796 (1973 to Sankyo), C.A. 78, 157861 (1973); T. Haneishi et al., J. Antibiot. 27, 386 (1974). Structures of methylenomycins A and B: eidem, ibid. 393. Crystal and molecular structure of (±)-A: B. H. Toder, A. B. Smith, J. Cryst. Mol. Struct. 8, 1 (1979). Stereospecific total synthesis of (±)-A: R. M. Scarborough et al., J. Am. Chem. Soc. 99, 7085 (1977); eidem, ibid. 102, 3904 (1980); and absolute configuration: K. Sakai et al., Tetrahedron Lett. 1979, 2365. Stereospecific total synthesis and absolute configuration of (+)-A: J. Jernow et al., J. Org. Chem. 44, 4210 (1979). Revised structure and total synthesis of B: eidem, ibid. 4212. Concise synthesis of B: M. Mikolajczyk, R. Zurawinski, Synlett 8, 575 (1991). Prepn of analogs of A and structure-activity correlations: T. Haneishi et al., J. Antibiot. 27, 400 (1974). Toxicity: eidem, ibid. 386. Methylenomycin A is the first example of an antibiotic in which all information required for synthesis is carried by a plasmid, SCP1: L. F. Wright, D. A. Hopwood, J. Gen. Microbiol. 95, 96 (1976). Review of biosynthesis: U. Hornemann, D. A. Hopwood, Antibiotics vol. IV, J. W. Corcoran, Ed. (Springer-Verlag, New York, 1981) pp 123-131. General review: A. Terehara et al., Heterocycles 13, 353-371 (1979).
