Regiocontrol in MnIII-mediated oxidative heterobicyclizations: access to the core skeletons of oroidin dimers

Xianghui Tan; Chuo Chen

doi:10.1002/anie.200601208

Regiocontrol in Mn^III-mediated oxidative heterobicyclizations: access to the core skeletons of oroidin dimers

Xianghui Tan, Chuo Chen

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

69 Scopus citations

Abstract

(Chemical Equation Presented) In control: A cyclization reaction of an allylic β-imidazolinonyl-β-ketoester 1 is carried out in a Mn ^III-promoted radical cascade. The reaction pathway (5-exo/6-endo or 5-exo/5-exo) can be directed to construct the central cyclopentyl and cyclohexenyl core skeletons (2 and 3) of two classes of oroidin dimers with regiocontrol. An oxidative rearrangement can also be used to convert 2 into 3. PG = protecting group.

Original language	English (US)
Pages (from-to)	4345-4348
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	45
Issue number	26
DOIs	https://doi.org/10.1002/anie.200601208
State	Published - Jun 26 2006

Keywords

Cascade reactions
Natural products
Radical reactions
Rearrangement
Synthetic methods

ASJC Scopus subject areas

Catalysis
General Chemistry

Access to Document

10.1002/anie.200601208

Cite this

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abstract = "(Chemical Equation Presented) In control: A cyclization reaction of an allylic β-imidazolinonyl-β-ketoester 1 is carried out in a Mn III-promoted radical cascade. The reaction pathway (5-exo/6-endo or 5-exo/5-exo) can be directed to construct the central cyclopentyl and cyclohexenyl core skeletons (2 and 3) of two classes of oroidin dimers with regiocontrol. An oxidative rearrangement can also be used to convert 2 into 3. PG = protecting group.",

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