Abstract
The structures of epohelmins A and B isolated as lanosterol synthase inhibitors from a fungal strain FKI-0929 were revised to be 1α-hydroxy-3α-(4′-oxoundec-(5′E)-enyl)-pyrrolizidine and 1β-hydroxy-3α-(4′-oxoundec-(5′E)-enyl)-pyrrolizidine, respectively, by comparison with spectral data of synthetic compounds.
Similar content being viewed by others
Article PDF
References
Sakano Y, Shibuya M, Matsumoto A, Takahashi Y, Tomoda H, Ōmura S, Ebizuka Y . Lanopylins A1, B1, A2 and B2, novel lanosterol synthase inhibitors from Streptomyces sp. K99-5041. J Antibiot 56: 817–826 ( 2003)
Sakano Y, Shibuya M, Yamaguchi Y, Masuma R, Tomoda H, Ōmura S, Ebizuka Y . Epohelmins A and B, novel lanosterol synthase inhibitors from a fungal strain FKI-0929. J Antibiot 57: 564–568 ( 2004)
Snider BB, Zhou J . Synthesis of lanopylin B1 . J Org Chem 70: 1087–1088 ( 2005)
Glass RS, Deardorff DR, Gains LH . Pyrrolizidine synthesis by intramolecular cyclization of a substituted azacyclooctane-4,5-oxide. Tetrahedron Lett 33: 2965–2968 ( 1978)
Subramanian T, Lin CC, Lin CC . Synthesis of oxazolidinyl azacycles via ring-closing olefin metathesis: a practical entry to the synthesis of deoxy-azasugars and hydroxypyrrolizidines. Tetrahedron Lett 42: 4079–4082 ( 2001)
Poon THW, Pringle K, Foote CS . Reaction of cyclooctenes with singlet oxygen. Trapping of a perepoxide intermediate. J Am Chem Soc 117: 7611–7618 ( 1995)
Snider BB, Gao X . Structure revision and syntheses of epohelmins A and B. Org Lett 7: 4419–4422 ( 2005)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Shibuya, M., Snider, B., Sakano, Y. et al. Revised Structures of Epohelmins A and B Isolated as Lanosterol Synthase Inhibitors from a Fungal Strain FKI-0929. J Antibiot 58, 599–601 (2005). https://doi.org/10.1038/ja.2005.82
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1038/ja.2005.82