Synthesis of the schweinfurthin hexahydroxanthene core through Shi epoxidation

Jeffrey D. Neighbors; Nolan R. Mente; Kelly D. Boss; Donald W. Zehnder; David F. Wiemer

doi:10.1016/j.tetlet.2007.11.086

Synthesis of the schweinfurthin hexahydroxanthene core through Shi epoxidation

Jeffrey D. Neighbors
, Nolan R. Mente
, Kelly D. Boss
, Donald W. Zehnder
, David F. Wiemer

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

26 Scopus citations

Abstract

Use of a Shi epoxidation for introduction of chirality in a key epoxide intermediate, together with revised protecting group tactics, has allowed an efficient synthesis of the hexahydroxanthene subunit common to the natural schweinfurthin F and the synthetic analogue 3-deoxyschweinfurthin B.

Original language	English (US)
Pages (from-to)	516-519
Number of pages	4
Journal	Tetrahedron Letters
Volume	49
Issue number	3
DOIs	https://doi.org/10.1016/j.tetlet.2007.11.086
State	Published - Jan 14 2008

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2007.11.086

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title = "Synthesis of the schweinfurthin hexahydroxanthene core through Shi epoxidation",

abstract = "Use of a Shi epoxidation for introduction of chirality in a key epoxide intermediate, together with revised protecting group tactics, has allowed an efficient synthesis of the hexahydroxanthene subunit common to the natural schweinfurthin F and the synthetic analogue 3-deoxyschweinfurthin B.",

author = "Neighbors, \{Jeffrey D.\} and Mente, \{Nolan R.\} and Boss, \{Kelly D.\} and Zehnder, \{Donald W.\} and Wiemer, \{David F.\}",

note = "Funding Information: Financial support from the Roy J. Carver Charitable Trust, the Children{\textquoteright}s Tumor Fund, the Breast Cancer Research Program (DAMD17-01-1-0276 and DAMD17-02-1-0423), an Oncology Research Training Award from the Holden Comprehensive Cancer Center{\textquoteright}s Institutional National Research Service Award (2 T32 CA79445) and the Predoctoral Training Program in the Pharmacological Sciences (2 T32 GM067795), is gratefully acknowledged. ",

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doi = "10.1016/j.tetlet.2007.11.086",

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volume = "49",

pages = "516--519",

journal = "Tetrahedron Letters",

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T1 - Synthesis of the schweinfurthin hexahydroxanthene core through Shi epoxidation

AU - Neighbors, Jeffrey D.

AU - Mente, Nolan R.

AU - Boss, Kelly D.

AU - Zehnder, Donald W.

AU - Wiemer, David F.

N1 - Funding Information: Financial support from the Roy J. Carver Charitable Trust, the Children’s Tumor Fund, the Breast Cancer Research Program (DAMD17-01-1-0276 and DAMD17-02-1-0423), an Oncology Research Training Award from the Holden Comprehensive Cancer Center’s Institutional National Research Service Award (2 T32 CA79445) and the Predoctoral Training Program in the Pharmacological Sciences (2 T32 GM067795), is gratefully acknowledged.

PY - 2008/1/14

Y1 - 2008/1/14

N2 - Use of a Shi epoxidation for introduction of chirality in a key epoxide intermediate, together with revised protecting group tactics, has allowed an efficient synthesis of the hexahydroxanthene subunit common to the natural schweinfurthin F and the synthetic analogue 3-deoxyschweinfurthin B.

AB - Use of a Shi epoxidation for introduction of chirality in a key epoxide intermediate, together with revised protecting group tactics, has allowed an efficient synthesis of the hexahydroxanthene subunit common to the natural schweinfurthin F and the synthetic analogue 3-deoxyschweinfurthin B.

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UR - https://www.scopus.com/pages/publications/37249017093#tab=citedBy

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DO - 10.1016/j.tetlet.2007.11.086

M3 - Article

AN - SCOPUS:37249017093

SN - 0040-4039

VL - 49

SP - 516

EP - 519

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 3

ER -

Synthesis of the schweinfurthin hexahydroxanthene core through Shi epoxidation

Abstract

All Science Journal Classification (ASJC) codes

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