Purines. LVII. Regioselective Alkylation of N^6,9-Disubstituted 8-Oxoadenines : Syntheses of the Sea Anemone Purine Caissarone and Some Positional Isomers and Analogues

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概要

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• The first total synthesis of caissarone hydrochloride (1), a constituent of the sea anemone Bunodosoma caissarum, has been accomplished via a two-step route starting from N^6,9-dimethyl-8-oxoadenine (3), which is obtainable from 9-methyladenine (5) through a four-step route. The key step in the synthesis is the regioselective methylation of 3 at N(3), which has been designed on the basis of a methylation study of N^6-benzyl-9-methyl-8-oxoadenine (11). Some positional isomers (19,24,and 31) and analogues (8,26,and 32) of 1 have also been synthesized. A ^1H-NMR spectroscopic study has suggested that the free base (23) of caissarone is capable of forming a hetero-base pair (such as 41) with 2', 3', 5'-tri-O-acetylguanosine (40) in Me_2SO-d_6.

• 公益社団法人日本薬学会の論文
• 1993-10-15

著者

• 斎藤 徹

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 藤井 澄三

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 藤井 澄三

  金沢大学薬学部

• 近澤 淳

  金沢大薬

• 近澤 淳

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 森 繁治

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 金井 妙

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 金井 妙

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 森 繁治

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 藤井 澄三

  Shinshu Univ. Nagano Jpn

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