Synthetic Studies on 8-Deoxyserratinine Type Alkaloids. Selective Cyclization of the 1,2-Cyclohexanediacetaldehyde Derivative by Intramolecular Aldol Condensation

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概要

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• In connection with the synthesis of 8-deoxyserratinine type alkaloids, the regioselective cyclization reaction of the 1,2-cyclohexanediacetaldehyde derivative (6) by intramolecular aldol condensation was investigated. The acetal (5) was stereoselectively prepared by two routes using the Diels-Alder reaction. The first route involved the Diels-Alder reaction of the dienophile (12), obtained from 8 via 9,10 and 11,with butadiene in the presence of 0.5 eq. AlCl_3 and acetalization of the adduct (13) to give 5 in 8% yield from 8. The second route involved conversion of the adduct (15), obtained by the Diels-Alder reaction of 8 with butadiene in the presence of 0.5 eq. BF_3・Et_2O, into 5 [22% yield based on the consumed dienophile (8)] via 16 and 17. The dialdehyde (6) was obtained from the cis-decalone derivative (5) via 18. Cyclization of 6 using excess morpholine-camphoric acid in dry Et_2O-HMPA and subsequent treatment with (EtO)_2POCH_2CN gave 21,which was suitable for our purpose, and 22 in a 25 : 1 ratio.

• 社団法人日本薬学会の論文
• 1980-04-25

著者

• 原山 尚

  Faculty of Pharmaceutical Sciences, Chiba University

• 犬伏 康夫

  Faculty of Pharmaceutical Sciences, Kyoto University

• 高谷 宗男

  京都大学薬学部

• 原山 尚

  Faculty Of Pharmaceutical Sciences Kyoto University

• 高谷 宗男

  Faculty of Pharmaceutical Sciences, Kyoto University

• 犬伏 康夫

  Faculty Of Pharmaceutical Sciences Kyoto University

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