A novel strategy for the key fully substituted cyclopentenedione moiety of madindolines via AlEt3-promoted tandem reductive rearrangement of α-hydroxy epoxides

Shuan Hu Gao; Yan Xing Jia; Xue Zhi Zhao; Yong Qiang Tu

doi:10.1002/cjoc.200690114

A novel strategy for the key fully substituted cyclopentenedione moiety of madindolines via AlEt₃-promoted tandem reductive rearrangement of α-hydroxy epoxides

Shuan Hu Gao^*
, Yan Xing Jia
, Xue Zhi Zhao
, Yong Qiang Tu

^*Corresponding author for this work

Lanzhou University

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

6 Scopus citations

Abstract

The fully substituted cyclopentenedione core of madindoline A (1) and B (2) as potent and selective inhibitor of IL-6 has been synthesized efficiently. The quaternary carbon center C-2′ was constructed on the basis of a newly developed AlEt₃-promoted tandem reductive rearrangement of α-hydroxy epoxides.

Original language	English
Pages (from-to)	595-597
Number of pages	3
Journal	Chinese Journal of Chemistry
Volume	24
Issue number	5
DOIs	https://doi.org/10.1002/cjoc.200690114
State	Published - May 2006
Externally published	Yes

Keywords

Epoxide rearrangement
Madindoline
Quaternary carbon
Tandem reaction
Total synthesis

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abstract = "The fully substituted cyclopentenedione core of madindoline A (1) and B (2) as potent and selective inhibitor of IL-6 has been synthesized efficiently. The quaternary carbon center C-2′ was constructed on the basis of a newly developed AlEt3-promoted tandem reductive rearrangement of α-hydroxy epoxides.",

keywords = "Epoxide rearrangement, Madindoline, Quaternary carbon, Tandem reaction, Total synthesis",

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year = "2006",

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AU - Gao, Shuan Hu

AU - Jia, Yan Xing

AU - Zhao, Xue Zhi

AU - Tu, Yong Qiang

PY - 2006/5

Y1 - 2006/5

N2 - The fully substituted cyclopentenedione core of madindoline A (1) and B (2) as potent and selective inhibitor of IL-6 has been synthesized efficiently. The quaternary carbon center C-2′ was constructed on the basis of a newly developed AlEt3-promoted tandem reductive rearrangement of α-hydroxy epoxides.

AB - The fully substituted cyclopentenedione core of madindoline A (1) and B (2) as potent and selective inhibitor of IL-6 has been synthesized efficiently. The quaternary carbon center C-2′ was constructed on the basis of a newly developed AlEt3-promoted tandem reductive rearrangement of α-hydroxy epoxides.

KW - Epoxide rearrangement

KW - Madindoline

KW - Quaternary carbon

KW - Tandem reaction

KW - Total synthesis

UR - https://www.scopus.com/pages/publications/33745028836

U2 - 10.1002/cjoc.200690114

DO - 10.1002/cjoc.200690114

M3 - 文章

AN - SCOPUS:33745028836

SN - 1001-604X

VL - 24

SP - 595

EP - 597

JO - Chinese Journal of Chemistry

JF - Chinese Journal of Chemistry

IS - 5

ER -

A novel strategy for the key fully substituted cyclopentenedione moiety of madindolines via AlEt₃-promoted tandem reductive rearrangement of α-hydroxy epoxides

Abstract

Keywords

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