Catalytic Dearomatization Approach to Quinolizidine Alkaloids: Five Step Total Synthesis of (±)-Lasubine II

Michael J. James; Niall D. Grant; Peter O’brien; Richard J. K. Taylor; William P. Unsworth

doi:10.1021/acs.orglett.6b03017

Catalytic Dearomatization Approach to Quinolizidine Alkaloids: Five Step Total Synthesis of (±)-Lasubine II

Michael J. James, Niall D. Grant, Peter O’brien, Richard J. K. Taylor, William P. Unsworth

Organic Chemistry Group

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

Abstract

A series of high-yielding silver(I)-catalyzed cyclization reactions of pyridine-, isoquinoline-, and pyrazine-ynones are described. The operationally simple and mild reaction conditions are a significant improvement over previously reported thermal cyclizations. The quinolizinone products were also used in a novel dearomatization strategy to prepare 0.53 g of the alkaloid lasubine II in five steps and 36% overall yield.

Original language	English
Pages (from-to)	6256-6259
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	24
DOIs	https://doi.org/10.1021/acs.orglett.6b03017
Publication status	Published - 30 Nov 2016

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https://pubs.acs.org/doi/10.1021/acs.orglett.6b03017

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title = "Catalytic Dearomatization Approach to Quinolizidine Alkaloids: Five Step Total Synthesis of (±)-Lasubine II",

abstract = "A series of high-yielding silver(I)-catalyzed cyclization reactions of pyridine-, isoquinoline-, and pyrazine-ynones are described. The operationally simple and mild reaction conditions are a significant improvement over previously reported thermal cyclizations. The quinolizinone products were also used in a novel dearomatization strategy to prepare 0.53 g of the alkaloid lasubine II in five steps and 36% overall yield.",

author = "James, {Michael J.} and Grant, {Niall D.} and Peter O{\textquoteright}brien and Taylor, {Richard J. K.} and Unsworth, {William P.}",

year = "2016",

month = nov,

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doi = "10.1021/acs.orglett.6b03017",

language = "English",

volume = "18",

pages = "6256--6259",

journal = "Organic Letters",

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T1 - Catalytic Dearomatization Approach to Quinolizidine Alkaloids

T2 - Five Step Total Synthesis of (±)-Lasubine II

AU - James, Michael J.

AU - Grant, Niall D.

AU - O’brien, Peter

AU - Taylor, Richard J. K.

AU - Unsworth, William P.

PY - 2016/11/30

Y1 - 2016/11/30

N2 - A series of high-yielding silver(I)-catalyzed cyclization reactions of pyridine-, isoquinoline-, and pyrazine-ynones are described. The operationally simple and mild reaction conditions are a significant improvement over previously reported thermal cyclizations. The quinolizinone products were also used in a novel dearomatization strategy to prepare 0.53 g of the alkaloid lasubine II in five steps and 36% overall yield.

AB - A series of high-yielding silver(I)-catalyzed cyclization reactions of pyridine-, isoquinoline-, and pyrazine-ynones are described. The operationally simple and mild reaction conditions are a significant improvement over previously reported thermal cyclizations. The quinolizinone products were also used in a novel dearomatization strategy to prepare 0.53 g of the alkaloid lasubine II in five steps and 36% overall yield.

U2 - 10.1021/acs.orglett.6b03017

DO - 10.1021/acs.orglett.6b03017

M3 - Article

SN - 1523-7052

VL - 18

SP - 6256

EP - 6259

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

Catalytic Dearomatization Approach to Quinolizidine Alkaloids: Five Step Total Synthesis of (±)-Lasubine II

Abstract

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