The Journal of organic chemistry

Total synthesis of natural bicyclic lactones (+)-dihydrocanadensolide,(±)-avenociolide, and (±)-isoavenociolide via tungsten-π-allyl complexes

MJ Chen, K Narkunan, RS Liu

文献索引：Chen, Ming-Jung; Narkunan, Kesavaram; Liu, Rai-Shung Journal of Organic Chemistry, 1999 , vol. 64, # 22 p. 8311 - 8318

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被引用次数: 43

摘要

A synthetic method using tungsten-π-allyl compounds is developed for total syntheses of natural bislactones including (+)-dihydrocanadensaolide (2),(±)-avenociolide (3), and (±)- isoavenociolide (4). Syntheses of these natural compounds are based on a common intermediate, trans-α-methylene butyrolactones bearing an anti-homoallylic alcohol. The kep steps in the syntheses involve an intramolecular alkoxycarbonylation of propargyltungsten ...