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

页码：908 / 911

页数：4

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