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- Title
First Total Synthesis of Piperenol B and Configuration Revision of the Enantiomers Piperenol B and Uvarirufol A.
- Authors
Fischer, Thomas C.; Cerra, Bruno; Fink, Michael J.; Rudroff, Florian; Horkel, Ernst; Mihovilovic, Marko D.
- Abstract
We report herein the first total synthesis of piperenol B, a polyoxygenated cyclohexene derivative with reported pharmacological activity isolated from Piper cubeb. The chiral building block for this synthetic approach is derived from microbial cis-ipso, ortho-dihydroxylation of sodium benzoate, which was optimized to the multi-ten-gram scale by reaction medium engineering. Final-stage deprotection of an acetonide was investigated in detail, leading to an efficient eight-step protocol for the synthesis of piperenol B with a total yield of 10 %. Most importantly, the previously assigned absolute configuration of piperenol B was revised and unequivocally established by 2D NMR analysis and the Mosher's ester method.
- Subjects
CHEMICAL synthesis; NATURAL products; BIOCATALYSIS; HYDROXYLATION; CYCLOHEXENE
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 7, p1464
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201403582