Total synthesis of (± )-trans-dihydronarciclasine through a highly endo-selective Diels-Alder cycloaddition of 3,5-dibromo-2-pyrone

In Ji Shin; Eun Sil Choi; Cheon Gyu Cho

doi:10.1002/anie.200604612

Total synthesis of (± )-trans-dihydronarciclasine through a highly endo-selective Diels-Alder cycloaddition of 3,5-dibromo-2-pyrone

In Ji Shin, Eun Sil Choi, Cheon Gyu Cho

Dept. of Fine Chemistry

Hanyang University

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

86 Scopus citations

Abstract

(Chemical Equation Presented) All essential functional groups in the natural product (±)-trans-dihydronarciclasine (1) were introduced with the correct relative configuration in a highly endo-selective Diels-Alder cycloaddition of 3,5-dibromo-2-pyrone with a styrene dienophile (see scheme). The total synthesis of 1 from these starting materials was completed in 11 steps and 15.8% overall yield.

Original language	English
Pages (from-to)	2303-2305
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	46
Issue number	13
DOIs	https://doi.org/10.1002/anie.200604612
State	Published - 2007

Keywords

Antitumor agents
Cycloaddition
Lactones
Natural products
Total synthesis

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KW - Total synthesis

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Total synthesis of (± )-trans-dihydronarciclasine through a highly endo-selective Diels-Alder cycloaddition of 3,5-dibromo-2-pyrone

Abstract

Keywords

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