Unusual transannular cyclization products of sarcophytoxide, a 14-membered marine cembranoid: Anomalous stereochemistry of epoxide-ketone rearrangement

被引：6
作者：
Nii, Keiji
Tagami, Keiko
Matsuoka, Keisuke
Munakata, Tatsuo
Ooi, Takashi
Kusumi, Takenori [1 ]
机构：
[1] Univ Tokushima, Grad Sch, Inst Hlth Biosci, Tokushima 7708505, Japan
[2] Tohwa Univ, Fac Engn, Dept Ind Chem, Fukuoka 8158510, Japan
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 14期
关键词：
D O I：
10.1021/ol0608404
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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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页码：2957 / 2960
页数：4
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