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Formal Total Synthesis of (−)-Jiadifenolide and Synthetic Studies toward seco-Prezizaane-Type Sesquiterpenes
Journal
Journal of Organic Chemistry
Volume
81
Number
22
Pages / Article-Number
11017-11034
Mesh terms
Carbon-13 Magnetic Resonance Spectroscopy; Cyclization; Proton Magnetic Resonance Spectroscopy; Sesquiterpenes, chemistry; Spectrometry, Mass, Electrospray Ionization; Stereoisomerism
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 electrophilic coupling partner was developed. In addition, synthetic approaches toward the related natural product (2 R )-hydroxy-norneomajucin, featuring a Mn-mediated radical cyclization for the tricycle assembly and a regioselective OH-directed C–H activation are presented.
