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Asymmetric synthesis of a tricyclic benzofuran motif: a privileged core structure in biologically active molecules.

Henrik Sundén ; Roger Olsson
Organic & biomolecular chemistry (1477-0539). Vol. 8 (2010), 21, p. 4831-3.
[Artikel, refereegranskad vetenskaplig]

An efficient synthetic strategy for the asymmetric synthesis of a hexahydrodibenzofuran core structure, with a quaternary stereogenic center, emerges by employing a chiral reduction using Corey's (S)-Me-CBS-oxazaborolidine reagent followed by a Mitsunobu reaction to set the stereochemistry. A Pd-mediated intramolecular Heck reaction concludes the tricyclic core structure. Finally, a Pd/C catalyzed reduction yields the target molecule in 21% overall yield over 6 steps.



Denna post skapades 2010-12-09. Senast ändrad 2017-09-14.
CPL Pubid: 130501

 

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Institutionen för kemi (2001-2011)

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Kemi

Chalmers infrastruktur