Journal
ORGANIC LETTERS
Volume 16, Issue 14, Pages 3760-3763Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol501631r
Keywords
-
Categories
Funding
- Alumni Association of Osaka University of Pharmaceutical Sciences
Ask authors/readers for more resources
The first synthesis of (-)-pericosine E (6), a metabolite of the Periconia byssoides OUPS-N133 isolated originally from the sea hare Aplysia kurodai, has been achieved. Efficient and regioselective synthetic procedures for the synthesis of key intermediates, anti- and syn-epoxides 9 and 10, were developed using an anti-epoxidation of diene 12 with TFDO and a bromohydrination of 12 with NIBS in CH3CN/H2O (2:3), respectively. In addition, comparison of the specific optical rotations between synthetic 6 and natural 6 elucidated that the naturally preferred enantiomer of pericosine E had the same absolute configuration as (-)-6 synthesized from chlorohydrin (-)-8 and anti-epoxide (+)-9.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available