Formation of the BC ring system of upenamide via a Staudinger/aza-Wittig reaction.
AUTHORS
Luo
ZZhushou ,
Peplowski
K Katherine ,
Sulikowski
GA Gary A .
Organic letters. 2007 11 22; 9(24).
5051-4
- PMID: 17973484[PubMed].
- PMCID: PMC2534099.
- NIHMSID: NIHMS63547
ABSTRACT
The BC ring system of upenamide was assembled using a stereoselective Diels-Alder reaction followed by a Staudinger/aza-Wittig/imine hydrolysis reaction. Stereoselective aldol coupling with an aldehyde that incorporates the DE ring system led to an advanced synthetic intermediate en route to the marine alkaloid upenamide.