A Synthesis of (+)-FR182877, Featuring Tandem Transannular Diels−Alder Reactions Inspired by a Postulated Biogenesis
Citations Over TimeTop 10% of 2002 papers
Abstract
An efficient biomimetic synthesis of the reported structure of the hexacyclic, cytotoxic secondary metabolite FR182877 is described. The successful route features the synthesis of a 19-membered ring carbocycle using two pi-allyl palladium(II)-mediated C-C bond-forming reactions. This polyunsaturated macrocycle undergoes tandem transannular Diels-Alder reactions that create five rings and seven stereogenic centers in one operation under mild conditions, representing the first double transannular Diels-Alder reaction. The absolute stereochemistry of the natural product is demonstrated to be opposite of that reported previously. Significant quantities of both enantiomers of this microtubule-stabilizing natural product and related structures are now available via this approach.
Related Papers
- A GEOMETRIC MEAN IN THE FURUTA INEQUALITY(2002)
- Susquehanna Chorale Spring Concert "Roots and Wings"(2017)
- Коммуникaтивно- прaгмaтический aнaлиз дипломaтических бумaг (нa основе вербaльных нот)(2018)
- → ФОРМИРОВAНИЕ ГОТОВНОСТИ БУДУЩИХ ПЕДAГОГОВ К ОРГAНИЗAЦИИ РAБОТЫ ПО РAЗВИТИЮ ВAЛЕОЛОГИЧЕСКОЙ КУЛЬТУРЫ ШКОЛЬНИКОВ(2023)