Synthesis of the cis-fused hexahydroxanthene system via cationic cascade cyclization

Jeffrey D. Neighbors; Joseph J. Topczewski; Dale C. Swenson; David F. Wiemer

doi:10.1016/j.tetlet.2009.04.052

Synthesis of the cis-fused hexahydroxanthene system via cationic cascade cyclization

Jeffrey D. Neighbors, Joseph J. Topczewski, Dale C. Swenson, David F. Wiemer

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15 Scopus citations

Abstract

The cis-fused hexahydroxanthene system can be obtained through a cascade cyclization initiated by Lewis acid-mediated epoxide opening and terminated by reaction with a MOM-protected phenol. Only a single diastereomer of the product was obtained with stereochemistry verified by diffraction analysis. This demonstrates the viability of this approach to natural products containing the cis-fused hexahydroxanthene skeleton, and supports preparation of more complex targets through a similar strategy.

Original language	English (US)
Pages (from-to)	3881-3884
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	27
DOIs	https://doi.org/10.1016/j.tetlet.2009.04.052
State	Published - Jul 8 2009

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "The cis-fused hexahydroxanthene system can be obtained through a cascade cyclization initiated by Lewis acid-mediated epoxide opening and terminated by reaction with a MOM-protected phenol. Only a single diastereomer of the product was obtained with stereochemistry verified by diffraction analysis. This demonstrates the viability of this approach to natural products containing the cis-fused hexahydroxanthene skeleton, and supports preparation of more complex targets through a similar strategy.",

author = "Neighbors, {Jeffrey D.} and Topczewski, {Joseph J.} and Swenson, {Dale C.} and Wiemer, {David F.}",

note = "Funding Information: Financial support in the form of a Shriner Fellowship (to J.J.T.) and from the Roy J. Carver Charitable Trust is gratefully acknowledged. Copyright: Copyright 2009 Elsevier B.V., All rights reserved.",

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AU - Swenson, Dale C.

AU - Wiemer, David F.

N1 - Funding Information: Financial support in the form of a Shriner Fellowship (to J.J.T.) and from the Roy J. Carver Charitable Trust is gratefully acknowledged. Copyright: Copyright 2009 Elsevier B.V., All rights reserved.

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AB - The cis-fused hexahydroxanthene system can be obtained through a cascade cyclization initiated by Lewis acid-mediated epoxide opening and terminated by reaction with a MOM-protected phenol. Only a single diastereomer of the product was obtained with stereochemistry verified by diffraction analysis. This demonstrates the viability of this approach to natural products containing the cis-fused hexahydroxanthene skeleton, and supports preparation of more complex targets through a similar strategy.

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Synthesis of the cis-fused hexahydroxanthene system via cationic cascade cyclization

Abstract

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