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Combining the Power of Ti III ‐Mediated Processes for Easy Access to Hydroxylated Polycyclic Terpenoids: Synthesis of Sesterstatin 1 and C–D Rings of Aspergilloxide
Author(s) -
Jiménez Tania,
Morcillo Sara P.,
MartínLasanta Ana,
ColladoSanz Daniel,
Cárdenas Diego J.,
Gansäuer Andreas,
Justicia José,
Cuerva Juan M.
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201201534
Subject(s) - terpenoid , prenylation , chemistry , stereochemistry , organic chemistry , enzyme
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.