46 Perhydrohistrionicotoxinの立体選択的合成研究
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Although synthetic studies on histrionicotoxins (HTX) which are toxic constituents of Neotropical arrow poison frogs of Dendrobates genus have been undertaken in many routes, we also have synthesized an important intermediate (35) of the toxin by a stereoselective manner outlined below. 1) Synthesis of the hydroxy-ester (17) A) Though treatment of the γ-acetoxy- orγ-t. butyldimethylsiloxy-α,β-unsat. esters (1a,1b,5) with ^nBu_2CuLi gave the reduced products (2,6), reaction with ^nBuCu-AlCl_3, a modified method of Yamamoto, yielded the α- and γ-substitution products. B) Although treatment of the ketones (9,13) with R_2CuLi provided the conjugate adducts in low yields, use of RCu-AlCl_3 yielded the 1,4-adducts in high yields (see Table). Hydrolysis of (10b) followed by acetylation gave the acetate (16), which was successively treated with NaOBr and CH_2N_2 to give (17). 2) Synthesis of a key intermediate (35) for perhydro-HTX. The THF-ester (18) derived from (17) was stereoselectively alkylated with allyl bromide to yield (21). The lactone (25), obtained by treatment of (21) with p. TsOH, was successively treated with OsO_4, (EtO)_2P(O)CHCO_2Et, and H_2/PtO_2 to afford the lactone-ester (27). The Dieckmann reaction of (27) with KH gave the keto-ester (28), which was decarboxylated to yield the ketone (29). Alternatively, the THF-ester (30), obtained from (21), was converted into the THF-ketone (33) by a similar procedure as above in a satisfactory yield. Oximation of (29) or (33) afforded the oxime (34), mp.56°. Beckmann rearrangement of (34) provided the lactam (35), mp. 164-165°, which is an intermediate for perhydro-HTX.
- 天然有機化合物討論会の論文
- 1980-09-10
著者
-
南方 宏之
(財)サントリー生有研
-
南方 宏之
Faculty Of Pharmaceutical Sciences Kyoto University
-
多賀 徹
京大・薬
-
井深 俊郎
Faculty Of Pharmaceutical Sciences Kyoto University
-
井深 俊郎
京大・薬
-
犬伏 康夫
京大・薬
-
犬伏 康夫
Faculty Of Pharmaceutical Sciences Kyoto University
-
南方 宏之
財団法人サントリー生物有機科学研究所
-
多賀 徹
京大・院薬・薬品分子構造
-
三井 義則
Faculty of Pharmaceutical Sciences, Kyoto University
-
南方 宏之
京大・薬
-
三井 義則
京大・薬
-
三井 義則
Faculty Of Pharmaceutical Sciences Kyoto University
-
南方 宏之
サントリー生物有機科学研
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