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

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

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...

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Veröffentlicht in:Organic letters 2016-12, Vol.18 (24), p.6256-6259
Hauptverfasser: James, Michael J, Grant, Niall D, O’Brien, Peter, Taylor, Richard J. K, Unsworth, William P
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container_end_page 6259
container_issue 24
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container_title Organic letters
container_volume 18
creator James, Michael J
Grant, Niall D
O’Brien, Peter
Taylor, Richard J. K
Unsworth, William P
description 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.
doi_str_mv 10.1021/acs.orglett.6b03017
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title Catalytic Dearomatization Approach to Quinolizidine Alkaloids: Five Step Total Synthesis of (±)-Lasubine II
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