Further Studies on Synthesis of the 12, 13-seco Norditerpenoid Alkaloids
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概要
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After a series of optimization for the reaction conditions (reagents, reaction temperature, etc.), treatment of the sulfonates 4, 8, 13 and 15 with 8% NaOH (room temperature, 24 h) via a semipinacol rearrangement afforded the corresponding C-nor compounds 5, 9, 12 and 16, as the major of a pair of epimer at C-16, to an excellent extent, in 95%, 92%, 100% and 90% yield, respectively. The 12,13-seco compounds 21 and 22 (23) were obtained in 20% and 60% yield, respectively, by treating 5 with Br_2-glacial HOAc (room temperature, 24 h). Treatment of the C-nor compounds 5 or 6, 16 or 17, and 28 from 10 with SOCl_2-anhydrous benzene (room temperature, overnight) afforded the 12, 13-seco compounds 24, 26 and 30 in 70% or 100%, 40% and 66% yield, respectively. When treatment of the C-nor compound 29 from 9 under same conditions gave the 12,13-seco products 30, 31 and 32 in 33%, 26% and 20% yield. When treating 21 or 24, and 26 with 5% KOH in EtOH afforded the 12, 13-seco compounds 25 and 27 quantitatively, respectively. The compound 31 converted to 30 quantitatively by treatment with Na_2CO_3 in MeOH. All of the new compounds were isolated and fully characterized.
- 公益社団法人日本薬学会の論文
- 2002-10-01
著者
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Chen Q‐h
Sichuan Univ. Chengdu Chn
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Chen Qiao-hong
Department Of Chemistry Of Medicinal Natural Products School Of Pharmacy West China University Of Me
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Wang Feng-peng
Department Of Chemistry Of Medicinal Natural Products And Key Laboratory Of Drug Targeting Of Educat
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Wang Feng-peng
Department Of Chemistry Of Medicinal Natural Products West China College Of Pharmacy Sichuan Univers
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Chen Qiao-hong
Deparmtment Of Chemistry Of Medicinal Natural Products West China Coll. Of Pharmacy Sichuan Univ.
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Wang Feng-Peng
Deparmtment of Chemistry of Medicinal Natural Products, West China College of Pharmacy, Sichuan University
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