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

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

Research output: Contribution to journalArticle

13 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)3881-3884
Number of pages4
JournalTetrahedron Letters
Volume50
Issue number27
DOIs
StatePublished - Jul 8 2009

Fingerprint

Lewis Acids
Stereochemistry
Cyclization
Epoxy Compounds
Phenol
Biological Products
Skeleton
Diffraction

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Neighbors, Jeffrey ; Topczewski, Joseph J. ; Swenson, Dale C. ; Wiemer, David F. / Synthesis of the cis-fused hexahydroxanthene system via cationic cascade cyclization. In: Tetrahedron Letters. 2009 ; Vol. 50, No. 27. pp. 3881-3884.
@article{459f16a04d054cc9ab69633f5c7f0542,
title = "Synthesis of the cis-fused hexahydroxanthene system via cationic cascade cyclization",
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 = "Jeffrey Neighbors and Topczewski, {Joseph J.} and Swenson, {Dale C.} and Wiemer, {David F.}",
year = "2009",
month = "7",
day = "8",
doi = "10.1016/j.tetlet.2009.04.052",
language = "English (US)",
volume = "50",
pages = "3881--3884",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "27",

}

Synthesis of the cis-fused hexahydroxanthene system via cationic cascade cyclization. / Neighbors, Jeffrey; Topczewski, Joseph J.; Swenson, Dale C.; Wiemer, David F.

In: Tetrahedron Letters, Vol. 50, No. 27, 08.07.2009, p. 3881-3884.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of the cis-fused hexahydroxanthene system via cationic cascade cyclization

AU - Neighbors, Jeffrey

AU - Topczewski, Joseph J.

AU - Swenson, Dale C.

AU - Wiemer, David F.

PY - 2009/7/8

Y1 - 2009/7/8

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=65549125834&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=65549125834&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2009.04.052

DO - 10.1016/j.tetlet.2009.04.052

M3 - Article

VL - 50

SP - 3881

EP - 3884

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 27

ER -