Synthesis of (+)-obtusenyne.

Journal article

An enantioselective synthesis of the halogenated medium-ring ether natural product (+)-obtusenyne is reported which uses the ring expansion of a seven-membered ketene acetal by means of a Claisen rearrangement to construct the core nine-membered oxygen heterocycle. The trans substituents across the ether linkage were established by using a transition-metal-catalyzed intramolecular hydrosilation reaction of an exo-cyclic enol ether. In addition, a formal synthesis of ent-obtusenyne from 2-deoxy-D-ribose is reported. A number of interesting points regarding the chemistry of medium-ring oxygen heterocycles are highlighted.

Authors: Mak, S; Curtis, N; Payne, A; Congreve, MS; Wildsmith, A

• Journal: Chemistry (Weinheim an der Bergstrasse, Germany)
• Volume: 14
• Issue: 9
• Pages: 2867-2885
• Publication date: 2008-01-01
• DOI: 10.1002/chem.200701567
• ISSN: 0947-6539
• Language: English