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

Hon Eong Ho; Michael J. James; Peter O’brien; Richard J. K. Taylor; William P. Unsworth

doi:10.1021/acs.orglett.8b00225

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

Hon Eong Ho, Michael J. James, Peter O’brien, Richard J. K. Taylor, William P. Unsworth

Organic Chemistry Group

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	1439-1443
Number of pages	5
Journal	Organic Letters
Volume	20
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.8b00225
Publication status	Published - 9 Feb 2018

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10.1021/acs.orglett.8b00225

https://pubs.acs.org/doi/10.1021/acs.orglett.8b00225

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

abstract = "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.",

author = "Ho, {Hon Eong} and James, {Michael J.} and Peter O{\textquoteright}brien and Taylor, {Richard J. K.} and Unsworth, {William P.}",

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language = "English",

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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 - Taylor, Richard J. K.

AU - Unsworth, William P.

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.

U2 - 10.1021/acs.orglett.8b00225

DO - 10.1021/acs.orglett.8b00225

M3 - Article

SN - 1523-7052

VL - 20

SP - 1439

EP - 1443

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

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

Abstract

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