Asymmetric synthesis of trans-p-menth-3-ene-1, 2, 8-triol, the monoterpene isolated from herbal plants. Issue 1 (2nd January 2020)

• Record Type: Journal Article
• Authors: Konishi, Shunsuke; Ogura, Yusuke; Takikawa, Hirosato; Watanabe, Hidenori
• Is Part Of: Bioscience, biotechnology, and biochemistry. Volume 84:Issue 1(2020)
• Page Start: 37
• Page End: 42
• Publication Date: 2020-01-02
• Subjects: Asymmetric synthesis -- asymmetric dihydroxylation -- monoterpene -- absolute configuration; Biotechnology -- Periodicals; Biochemistry -- Periodicals; 660.6
• DOI: 10.1080/09168451.2019.1671789
• Languages: English
• ISSNs: 0916-8451

Abstract

ABSTRACT: The monoterpene, trans-p -menth-3-ene-1, 2, 8-triol, is a naturally occurring alcohol isolated from several herbal plants. In the present work, the asymmetric synthesis of both enantiomers of this natural product was achieved using Sharpless asymmetric dihydroxylation as the key step. A reversal of enantiofacial selectivity was observed in the asymmetric dihydroxylation. Graphical abstract: : The first asymmetric synthesis of trans-p -menth-3-ene-1, 2, 8-triol was achieved.