Unusual transannular cyclization products of sarcophytoxide, a 14-membered marine cembranoid: anomalous stereochemistry of epoxide-ketone rearrangement |
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Authors: | Nii Keiji Tagami Keiko Matsuoka Keisuke Munakata Tatsuo Ooi Takashi Kusumi Takenori |
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Affiliation: | Institute of Health Biosciences, The University of Tokushima Graduate School, Japan. |
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Abstract: | [reaction: see text] Treatment 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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