title: ORGANIC SYNTHESIS. Comment on "Asymmetric syntheses of sceptrin and massadine and evidence for biosynthetic enantiodivergence".
abstract: Ma et al. (Reports, 10 October 2014, p. 219) report asymmetric syntheses of sceptrin and massadine and, through a stereochemical reassignment, claim to "uncover enantiodivergence as a new biosynthetic paradigm for natural products." We challenge and clarify this claim with relevant examples from the literature of this well-known phenomenon of enantiodivergent congener biosynthesis within the same producing organism.
authors.affiliation: Life Sciences Institute and Departments of Medicinal Chemistry, Microbiology and Immunology, and Chemistry, University of Michigan, Ann Arbor, MI 48109, USA.
authors.forename: David H
authors.initials: DH
authors.lastname: Sherman
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan.
authors.forename: Sachiko
authors.initials: S
authors.lastname: Tsukamoto
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA. The University of Colorado Cancer Center, Aurora, CO 80045, USA. robert.williams@colostate.edu.
authors.forename: Robert M
authors.initials: RM
authors.lastname: Williams
mesh_terms: D000818:Animals; D061565:Cycloaddition Reaction; D011161:Porifera / Q000378:metabolism*; D011758:Pyrroles / Q000138:chemical synthesis*
chemical_list: D011758:Pyrroles