Formal Total Synthesis of (−)-Jiadifenolide and Synthetic Studies toward seco-Prezizaane-Type Sesquiterpenes
JOURNAL OF ORGANIC CHEMISTRY(2016)
Abstract
Synthetic studies toward highly oxygenated seco-prezizaane sesquiterpenes are reported, which culminated in a formal total synthesis of the neurotrophic agent (-)-jiadifenolide. For the construction of the tricyclic core structure, an unusual intramolecular and diastereoselective Nozaki-Hiyama-Kishi reaction involving a ketone as electro-philic coupling partner was developed. In addition, synthetic approaches toward the related natural product (2R)-hydroxy-norneomajucin, featuring a Mn-mediated radical cyclization for the tricycle assembly and a regioselective OH-directed C-H activation are presented.
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Key words
total synthesis,formal total synthesis,prezizaane-type
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