Synthesis and structure of the marine ascidian 8-oxoadenine aplidiamine

DOI: 10.1248/cpb.47.1297

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Chemical and Pharmaceutical Bulletin p. 1297 - 1300 (1999)

Update date:2022-08-05

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Authors:

Itaya, Taisuke

Hozumi, Yoshitaka

Kanai, Tae

Ohta, Tomihisa

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Article abstract of DOI:10.1248/cpb.47.1297

Alkylation of 8-oxoadenosine (13) with 4-benzyloxy-3,5-dibromobenzyl bromide (20), followed by Dimroth rearrangement and acid hydrolysis, provided N-(3,5-dibromo-4-hydroxybenzyl)-8-oxoadenosine (15). The 2'- deoxy version of this reaction sequence accomplished the first synthesis of N-(3,5-dibromo-4- hydroxybenzyl)-8-oxoadenine (16), which is the correct expression for marine ascidian purine aplidiamine.

Full text of DOI:10.1248/cpb.47.1297

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