Highly Oxygenated Diterpenoids Associated to the Central Nervous System : Syntheses of Salvinorin and Forskolin
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概要
- 論文の詳細を見る
Total synthesis of salvinorin A (1), a densely functionalized neoclerodane diterpenoid, having the most potent hallucinogenic activity and a selective κ–opioid agonist, has been completed in 20 steps starting from enantiomerically–pure Wieland–Miescher ketone derivative 23. Subsequently, alternative total synthesis of salvinorin A (1) has been developed via palladium–catalyzed double carbonylation to bis–enol triflate followed by samarium diiodide–mediated double conjugate reduction in 13 steps. Forskolin (2), a highly oxygenated labdane diterpenoid and an activator of adenylate cyclase, has been synthesized in 12 steps and 12% overall yield from ptychantin A (62), which has been isolated from liverwort Ptychanthus striatus in sufficient yield. Tuning of the synthetic pathway enabled more expedient synthesis of forskolin (2) in 11 steps with 17% overall yield from ptychantins A (62) and B (63). In addition, synthesis of 1,9–dideoxyforskolin (3), an inhibitor of glucose transporter, has been accomplished in 8 steps and 37% overall yield from ptychantin A (62).
- 社団法人 有機合成化学協会の論文
- 2009-11-01
著者
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Nozawa Masato
Graduate School Of Science And Technology Niigata University
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Hagiwara Hisahiro
Graduate School Of Science And Technology Niigata University
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- Highly Oxygenated Diterpenoids Associated to the Central Nervous System : Syntheses of Salvinorin and Forskolin