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.
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.