Abstract
A total synthesis of all-E-citreomontanin, produced by Pencillium pedemontanum and believed to be the putative precursor of citreoviridin and citreoviridinol, involving successive epoxidations of its terminal triene portion, is described. Elaboration of the pyrone 9a to the phosphonium salt 13b was smoothly accomplished via the key pyrone aldehyde intermediates 10 and 12. The all-E-trienal 7 required for Wittig coupling with compound 13b was readily produced from the aldehyde 14 by use of two successive stereoselective Wittig olefination reactions involving the stabilised phosphorane 15; i.e., 14+15→16, and 17+15→18. A Wittig coupling reaction between the ylide 8 derived from 13b and the trienal 7 then produced the all-E-polyene 1, as an orange solid, which was identical with citreomontanin isolated from P. pedemontanum.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 1
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
