Exploration of an epoxidation–ring-opening strategy for the synthesis of lyconadin A and discovery of an unexpected Payne rearrangement

Exploration of an epoxidation–ring-opening strategy for the synthesis of lyconadin A and discovery of an unexpected Payne rearrangement

In the context of synthetic efforts targeting the alkaloid lyconadin A, scalemic epoxide 25 was prepared by a highly stereoselective sequence involving a Myers alkylation and a Shi epoxidation. Ring-opening of this epoxide with a vinylcopper complex afforded alcohol 26 instead of the expected produc...

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Bibliographic Details
Main Authors: Brad M. Loertscher, Yu Zhang, Steven L. Castle
Format: Article
Language:English
Published: Beilstein-Institut 2013-06-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
Lewis acid
lyconadin A
Myers alkylation
Payne rearrangement
Shi epoxidation
Online Access:https://doi.org/10.3762/bjoc.9.132
Description
Summary:In the context of synthetic efforts targeting the alkaloid lyconadin A, scalemic epoxide 25 was prepared by a highly stereoselective sequence involving a Myers alkylation and a Shi epoxidation. Ring-opening of this epoxide with a vinylcopper complex afforded alcohol 26 instead of the expected product 27. An unusual Lewis acid promoted Payne rearrangement of an α-trityloxy epoxide is proposed to account for this outcome.
ISSN:1860-5397

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