Ag(I)-Catalyzed Synthesis of Azabicyclic Alkaloid Frameworks from Ketimine-Tethered Ynones: Total Synthesis of Indolizidine 209D

TY - JOUR

T1 - Ag(I)-Catalyzed Synthesis of Azabicyclic Alkaloid Frameworks from Ketimine-Tethered Ynones

T2 - Total Synthesis of Indolizidine 209D

AU - Ho, Hon Eong

AU - James, Michael J

AU - O'Brien, Peter

AU - Unsworth, William P

AU - Taylor, Richard John Kenneth

N1 - © 2018 American Chemical Society. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details

PY - 2018/2/9

Y1 - 2018/2/9

N2 - An efficient Ag(I)-catalyzed π-acid activation method for the cyclization of cyclic ketimine-tethered ynones is reported. Various nitrogen-containing scaffolds commonly found in bioactive alkaloids can be prepared in high yields, and the utility of the method is demonstrated by a formal synthesis of (±)-lasubine II and in a short total synthesis of (±)-indolizidine 209D.

AB - An efficient Ag(I)-catalyzed π-acid activation method for the cyclization of cyclic ketimine-tethered ynones is reported. Various nitrogen-containing scaffolds commonly found in bioactive alkaloids can be prepared in high yields, and the utility of the method is demonstrated by a formal synthesis of (±)-lasubine II and in a short total synthesis of (±)-indolizidine 209D.

KW - Journal Article

U2 - 10.1021/acs.orglett.8b00225

DO - 10.1021/acs.orglett.8b00225

M3 - Article

C2 - 29425045

SN - 1523-7060

SP - 1439

EP - 1443

JO - Organic Letters

JF - Organic Letters

ER -