ORGANIC SYNTHESIS. Comment on "Asymmetric syntheses of sceptrin and massadine and evidence for biosynthetic enantiodivergence"

David H Sherman; Sachiko Tsukamoto; Robert M Williams

doi:10.1126/science.aaa9349

ORGANIC SYNTHESIS. Comment on "Asymmetric syntheses of sceptrin and massadine and evidence for biosynthetic enantiodivergence"

Science. 2015 Jul 10;349(6244):149. doi: 10.1126/science.aaa9349. Epub 2015 Jul 9.

Authors

David H Sherman¹, Sachiko Tsukamoto², Robert M Williams³

Affiliations

¹ Life Sciences Institute and Departments of Medicinal Chemistry, Microbiology and Immunology, and Chemistry, University of Michigan, Ann Arbor, MI 48109, USA.
² Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan.
³ 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.

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.

Publication types

Research Support, N.I.H., Extramural
Comment

MeSH terms

Animals
Cycloaddition Reaction*
Porifera / metabolism*
Pyrroles / chemical synthesis*

Substances

Pyrroles

Abstract

Publication types

MeSH terms

Substances

Grants and funding