Published June 26, 2012 | Version v1
Journal article Open

First Total Synthesis of Paracaseolide A

  • 1. University of Crete

Description

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.

Notes

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see: http://pubs.acs.org/page/policy/articlesonrequest/index.html

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Funding

SINOXYGEN – Advancing the Green Chemistry of Singlet Oxygen and Applying it to Synthetic Challenges 277588
European Commission