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Formal Total Synthesis of (−)-Jiadifenolide and Synthetic Studies toward seco-Prezizaane-Type Sesquiterpenes

Gomes, José and Daeppen, Christophe and Liffert, Raphael and Roesslein, Joel and Kaufmann, Elias and Heikinheim, Annakasia and Neuburger, Markus and Gademann, Karl. (2016) Formal Total Synthesis of (−)-Jiadifenolide and Synthetic Studies toward seco-Prezizaane-Type Sesquiterpenes. Journal of Organic Chemistry, 81 (22). pp. 11017-11034.

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Official URL: http://edoc.unibas.ch/53476/

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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.
Faculties and Departments:05 Faculty of Science > Departement Chemie
05 Faculty of Science > Departement Chemie > Former Organization Units Chemistry > Organische Chemie (Gademann)
UniBasel Contributors:Gademann, Karl and Gomes, José Rui and Daeppen, Christophe and Liffert, Raphael and Kaufmann, Elias and Neuburger, Markus
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:American Chemical Society
ISSN:0022-3263
e-ISSN:1520-6904
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:25 Jan 2017 15:38
Deposited On:25 Jan 2017 15:38

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