Stereoselective Synthesis of the C25-C36 Segment of Arenicolides A and B: Determination of the Configuration of the Trisubstituted Epoxide

被引：5
|
作者：
Nagumo, Shinji [1 ]
Nakano, Taeko [1 ]
Hata, Kyomi [1 ]
Mizukami, Megumi [2 ]
Miyashita, Masaaki [1 ]
机构：
[1] Kogakuin Univ, Dept Appl Chem, Tokyo 1920015, Japan
[2] Hokkaido Pharmaceut Univ, Sch Pharm, Otaru, Hokkaido 0470264, Japan
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 05期
关键词：
1,3-DIOL ACETONIDES; STEREOCHEMISTRY; CATALYST; ALCOHOLS; ACID;
D O I：
10.1021/ol902750e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two diastereomeric epoxides 4a and 4b corresponding to the C-25-C-36 fragment of arenicolides A and B were synthesized in a stereoselective manner involving the Pd(0)-catalyzed stereospecific methoxy substitution reaction of epoxy unsaturated ester 6 with B(OMe)(3) as the key step. Comparison of the H-1 NMR spectra of the synthetic compounds with that of arenicolide A revealed that the configuration of the epoxide in arenicolides A and B is 30R and 31R.
引用
收藏
页码：908 / 911
页数：4
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