Subscribe to RSS
DOI: 10.1055/s-2007-968387
Synthesis of Amphidinolide E
Contributor(s):Philip Kocienski, Fiona BlackThe Scripps Research Institute, Florida, Jupiter, USA
Total Synthesis of Amphidinolide E
J. Am. Chem. Soc. 2006, 128: 15960-15961
Publication History
Publication Date:
24 April 2007 (online)
Key words
[3+2] annulation - Johnson-Claisen rearrangement - Yamaguchi lactonization
Significance
The cis-tetrahydrofuran ring of amphidinolide A is synthesized using a highly diastereoselective [3+2] annulation reaction. Deft use of Fe(CO)3 as protecting group led to successful esterification of a hindered secondary alcohol. For an alternative synthesis of amphidinolide A, see: E. Lee and co-workers Angew. Chem. Int. Ed. 2006, 45, 8019-8021.
Comment
Aldehyde A was treated with allyl silane B in the presence of BF3·OEt2 to generate C via a [3+2] annulation reaction. The diene of acid E was complexed with -Fe(CO)3 to prevent alkene migration under Yamaguchi esterification conditions. Use of the diastereoisomeric complex E in the esterification-decomplexation sequence failed to provide F.