By the same authors

From the same journal

From the same journal

Catalytic Asymmetric Total Syntheses of (R)-Bgugaine and (R)-Irnidine

Research output: Contribution to journalSpecial issuepeer-review

Published copy (DOI)

Author(s)

Department/unit(s)

Publication details

JournalTetrahedron
DateAccepted/In press - 19 Nov 2020
DateE-pub ahead of print - 28 Nov 2020
DatePublished (current) - 8 Jan 2021
Issue number8
Volume78
Number of pages9
Pages (from-to)1-9
Early online date28/11/20
Original languageEnglish

Abstract

An enantioselective total synthesis of (R)-bgugaine and the first enantioselective total synthesis of (R)-irnidine are reported. The key steps are the asymmetric ‘clip-cycle’ formation of the pyrrolidine ring in 94:6 e.r., which is common to both natural products, followed by Liebeskind–Srogl coupling and Wolf-Kishner reduction. The route yields (R)-bgugaine and (R)-irnidine in 6 steps and in overall yields of 33% and 18% respectively.

Bibliographical note

Invited submission to the Prof. Richard Taylor Special Issue

©2020 Elsevier Ltd. All rights reserved.This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy.

Research outputs

Projects

Discover related content

Find related publications, people, projects, datasets and more using interactive charts.

View graph of relations