First Total Synthesis of Paracaseolide A

descriptionPublicationkeyboard_double_arrow_right Article 26 Jun 2012 English Publisher:American Chemical Society (ACS)Journal:Organic Letters, volume 14, pages 3,565-3,567 (issn: 1523-7060, eissn: 1523-7052,

Copyright policy )Funded by:EC | SINOXYGEN

Authors: Noutsias; D.; Vassilikogiannakis; G.;

doi: 10.1021/ol301481t

pmid: 22734450

First Total Synthesis of Paracaseolide A

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Abstract

The first total synthesis of the paracaseolide A, a very unusual tetraquinane oxa-cage bislactone recently isolated from the mangrove Sonneratia paracaseolaris, has been achieved. The final step and culmination of the eight-step synthetic sequence is a [4 + 2] dimerization of a 4-hydroxybutenolide, generated by singlet oxygen-mediated oxidation of a furan precursor.

Related Organizations

University of Crete
Greece

Keywords

Molecular Structure, Singlet Oxygen, Singlet oxygen, Photochemistry, Total synthesis, Stereoisomerism, 4-Butyrolactone, Paracaseolide A, Furan oxidation, Diels-Alder reaction, Dimerization, Oxidation-Reduction

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