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

TY - JOUR

T1 - Catalytic Asymmetric Total Syntheses of (R)-Bgugaine and (R)-Irnidine

AU - Clarke, Paul Andrew

AU - Maddocks, Christopher

N1 - 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.

PY - 2021/1/8

Y1 - 2021/1/8

N2 - 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.

AB - 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.

U2 - 10.1016/j.tet.2020.131789

DO - 10.1016/j.tet.2020.131789

M3 - Special issue

SN - 0040-4020

VL - 78

SP - 1

EP - 9

JO - Tetrahedron

JF - Tetrahedron

IS - 8

M1 - 131789

ER -