Unusual Transannular Cyclization Products of Sarcophytoxide, a 14-Membered Marine Cembranoid: Anomalous Stereochemistry of Epoxide−Ketone Rearrangement
2006; American Chemical Society; Volume: 8; Issue: 14 Linguagem: Inglês
10.1021/ol0608404
ISSN1523-7060
AutoresKeiji Nii, Keiko Tagami, K. Matsuoka, Tatsuo Munakata, Takashi Ooi, Takenori Kusumi,
Tópico(s)Marine Biology and Environmental Chemistry
ResumoTreatment of sarcophytoxide with trimethylsilyl trifluoromethanesulfonate afforded an aromatic ketone as an unusual cyclization product. The modified Mosher's method and X-ray analysis performed on the aromatic ketone revealed that it is a 4:1 mixture of 8(R)- and 8(S)-enantiomers. It also suggested that the precursor ketone has 8(R)-configuration, which is contradictory to that expected from the ordinary epoxide−ketone rearrangement.
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