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


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

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 (2R)-hydroxy-norneomajucin, featuring a Mn-mediated radical cyclization for the tricycle assembly and a regioselective OH-directed C–H activation are presented.

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 (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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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2016
Deposited On:09 Feb 2017 15:35
Last Modified:18 Apr 2018 11:48
Publisher:American Chemical Society (ACS)
ISSN:0022-3263
Funders:SNF (200020_163151 and 200021_144028).
OA Status:Green
Publisher DOI:https://doi.org/10.1021/acs.joc.6b02039
Project Information:
  • : FunderSNSF
  • : Grant ID
  • : Project TitleSNF (200020_163151 and 200021_144028).

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