Enantioselective synthesis of (+)-petromyroxol, enabled by rhodium-catalyzed denitrogenation and rearrangement of a 1-sulfonyl-1,2,3-triazole

Boyer, A. (2015) Enantioselective synthesis of (+)-petromyroxol, enabled by rhodium-catalyzed denitrogenation and rearrangement of a 1-sulfonyl-1,2,3-triazole. Journal of Organic Chemistry, 80(9), pp. 4771-4775. (doi: 10.1021/acs.joc.5b00399) (PMID:25891197)

Abstract

Petromyroxol is a non-racemic mixture of enantiomeric oxylipids isolated from water conditioned with larval sea lamprey. The (+)-antipode exhibits interesting biological properties but only 1 mg was isolated from >100000 L of water. Recently, transition metal-catalyzed denitrogenation of 1-sulfonyl-1,2,3-triazoles has emerged as a powerful strategy for the synthesis of value-added products, including efficient diastereocontrolled construction of tetrahydrofurans. This methodology enabled the rapid development of the first synthesis of (+)-petromyroxol in 9 steps and 20% overall yield from a readily accessible starting material.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Boyer, Dr Alistair
• Authors: Boyer, A.
• Subjects: Q Science > QD Chemistry
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Journal of Organic Chemistry
• Publisher: American Chemical Society
• ISSN: 0022-3263
• ISSN (Online): 1520-6904
• Published Online: 20 April 2015
• Copyright Holders: Copyright © 2015 American Chemical Society
• First Published: First published in Journal of Organic Chemistry 80(9):4771-4775
• Publisher Policy: Reproduced in accordance with the copyright policy of the publisher