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Combining the Power of TiIII-Mediated Processes for Easy Access to Hydroxylated Polycyclic Terpenoids: Synthesis of Sesterstatin 1 and C-D Rings of Aspergilloxide
Ist Teil von
Chemistry : a European journal, 2012-10, Vol.18 (40), p.12825-12833
Ort / Verlag
Weinheim: WILEY-VCH Verlag
Erscheinungsjahr
2012
Link zum Volltext
Quelle
Wiley Online Library Journals Frontfile Complete
Beschreibungen/Notizen
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.
Doing it the easy way: Polyhydroxylated terpenoids are accessed through two titanocene(III)‐mediated reactions: a “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 a subsequent radical cyclisation. This methodology is used in the first total synthesis of sesterstatin 1 and a model compound of the C–D rings of aspergilloxide (see scheme).