Asymmetric synthesis and biosynthetic implications of (+)-fusarisetin A

Jun Yin; Cheng Wang; Lili Kong; Shujun Cai; Shuanhu Gao

doi:10.1002/anie.201202455

Asymmetric synthesis and biosynthetic implications of (+)-fusarisetin A

Jun Yin, Cheng Wang, Lili Kong, Shujun Cai, Shuanhu Gao

School of Chemistry and Molecular Engineering

East China Normal University

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

82 Scopus citations

Abstract

Starting from equisetin, the asymmetric synthesis of (+)-fusarisetin A has been accomplished in a one-pot transformation including a biomimetic oxidation and an intramolecular Diels-Alder/Roskamp reaction. Peroxyfusarisetin is proposed as a plausible biosynthetic intermediate based on studies of the oxidation of equisetin.

Original language	English
Pages (from-to)	7786-7789
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	31
DOIs	https://doi.org/10.1002/anie.201202455
State	Published - 27 Jul 2012

Keywords

biosynthesis
natural products
peroxides
radical reactions
total synthesis

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10.1002/anie.201202455

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abstract = "Starting from equisetin, the asymmetric synthesis of (+)-fusarisetin A has been accomplished in a one-pot transformation including a biomimetic oxidation and an intramolecular Diels-Alder/Roskamp reaction. Peroxyfusarisetin is proposed as a plausible biosynthetic intermediate based on studies of the oxidation of equisetin.",

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author = "Jun Yin and Cheng Wang and Lili Kong and Shujun Cai and Shuanhu Gao",

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AU - Yin, Jun

AU - Wang, Cheng

AU - Kong, Lili

AU - Cai, Shujun

AU - Gao, Shuanhu

PY - 2012/7/27

Y1 - 2012/7/27

N2 - Starting from equisetin, the asymmetric synthesis of (+)-fusarisetin A has been accomplished in a one-pot transformation including a biomimetic oxidation and an intramolecular Diels-Alder/Roskamp reaction. Peroxyfusarisetin is proposed as a plausible biosynthetic intermediate based on studies of the oxidation of equisetin.

AB - Starting from equisetin, the asymmetric synthesis of (+)-fusarisetin A has been accomplished in a one-pot transformation including a biomimetic oxidation and an intramolecular Diels-Alder/Roskamp reaction. Peroxyfusarisetin is proposed as a plausible biosynthetic intermediate based on studies of the oxidation of equisetin.

KW - biosynthesis

KW - natural products

KW - peroxides

KW - radical reactions

KW - total synthesis

UR - https://www.scopus.com/pages/publications/84864403252

U2 - 10.1002/anie.201202455

DO - 10.1002/anie.201202455

M3 - 文章

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AN - SCOPUS:84864403252

SN - 1433-7851

VL - 51

SP - 7786

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 31

ER -

Asymmetric synthesis and biosynthetic implications of (+)-fusarisetin A

Abstract

Keywords

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