- Synthetic transformation of ptychantin into forskolin and 1,9-dideoxyforskolin
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Forskolin (1), a highly oxygenated labdane diterpenoid and an activator of adenylate cyclase, has been synthesized in 12 steps and 12% overall yield from ptychantin A (4), which has been isolated from liverwort Ptychanthus striatus in good yield. The 1α-hydroxy group was furnished by stereoselective reduction of the corresponding carbonyl group by sodium in t-BuOH. The 9α-hydroxy group was introduced stereoselectively by epoxidation of Δ9.11-enolether. 1,9-Dideoxyforskolin (2), an inhibitor of glucose transporter, has been synthesized in 8 steps and 37% overall yield. The hydroxy group at C-1 was removed by solid-state thicarbonylimidazolation and subsequent radical cleavage.
- Hagiwara, Hisahiro,Takeuchi, Fumihide,Kudou, Masaru,Hoshi, Takashi,Suzuki, Toshio,Hashimoto, Toshihiro,Asakawa, Yoshinori
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p. 4619 - 4624
(2007/10/03)
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- First synthesis of 1,9-dideoxyforskolin from ptychantin A
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1,9-Dideoxyforskolin 2 has been synthesized starting from ptychantin A 3.
- Hagiwara, Hisahiro,Takeuchi, Fumihide,Hoshi, Takashi,Suzuki, Toshio,Hashimoto, Toshihiro,Asakawa, Yoshinori
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p. 2305 - 2306
(2007/10/03)
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