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Synthesis of the structures proposed for natural butanolides piliferolides A and C |
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| Authors: | Jing Guan Zhi-Bin ZhenYang Zou Zheng-Yu Yue Ping Jiang Yan LiYikang Wu |
| Affiliation: | a State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China b School of Chemistry and Materials, Heilongjiang University, Harbin 150080, China c Ministry-of-Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules and School of Chemistry and Chemical Engineering, Hubei University, Wuhan 430062, China |
| Abstract: | The structures proposed for natural butanolides piliferolides A and C have been synthesized. The allylic and lactone stereogenic centers in the target structures were derived from d-mannitol, while that near the side-chain terminal was taken from (R)-propylene oxide. The synthetic samples helped to reveal that a signal at around δ 2.0 ppm was missing in the 1H NMR data listing for the structures proposed for natural piliferolides, whereas the δ 29.7 ppm signal in the 13C NMR reported for the structure proposed for natural piliferolide C most likely stemmed from the impurities in the chromatography solvent. |
| Keywords: | Butanolides Natural products Structure elucidation Epoxides Metathesis |
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