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- Title
Combining the Power of Ti<sup>III</sup>-Mediated Processes for Easy Access to Hydroxylated Polycyclic Terpenoids: Synthesis of Sesterstatin 1 and C-D Rings of Aspergilloxide.
- Authors
Jiménez, Tania; Morcillo, Sara P.; Martín-Lasanta, Ana; Collado-Sanz, Daniel; Cárdenas, Diego J.; Gansäuer, Andreas; Justicia, José; Cuerva, Juan M.
- Abstract
A straightforward access to polyhydroxylated terpenoids based on two key titanocene(III)-mediated reactions is presented: the 'head-to-tail' Barbier-type addition of prenyl chlorides to α,β-unsaturated aldehydes, which allows the introduction of hydroxy groups at desirable positions of the acyclic precursor, and the subsequent bioinspired radical cyclisation. This methodology has been also used in the first total synthesis of pentacyclic sesterstatin 1 and a model compound of the C-D rings of aspergilloxide.
- Publication
Chemistry - A European Journal, 2012, Vol 18, Issue 40, p12825
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201201534