Stereoselective total synthesis of (±)-parthenolide and (±)-7-epi-parthenolide

The total synthesis of (±)-parthenolide and (±)-7-epi-parthenolide starting from readily available limonene has been achieved with high stereoselectivity. The key synthetic features include (i) a ring expansion reaction, Oxy-Cope rearrangement to construct the medium-sized carbocycle on large scale...

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Bibliographic Details
Published in:Tetrahedron 2016-07, Vol.72 (29), p.4346-4354
Main Authors: Li, Liang, Pan, Xuan, Guan, Baohe, Liu, Zhanzhu
Format: Article
Language:English
Subjects:
Analogs
Construction
Lactones
Parthenolide
Stereoisomers
Stereoselective
Stereoselectivity
Substrate-controlled
Synthesis
Tetrahedrons
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Summary:The total synthesis of (±)-parthenolide and (±)-7-epi-parthenolide starting from readily available limonene has been achieved with high stereoselectivity. The key synthetic features include (i) a ring expansion reaction, Oxy-Cope rearrangement to construct the medium-sized carbocycle on large scale and (ii) substrate-controlled stereoselective introduction of the lactone and epoxy moiety at a late stage, providing a flexible method to synthesize PTL analogs. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2016.05.074