Synthesis and structure of the marine ascidian 8-oxoadenine aplidiamine

Authors
Itaya, T Hozumi, Y Kanai, T Ohta, T
Citation
T. Itaya et al., Synthesis and structure of the marine ascidian 8-oxoadenine aplidiamine, CHEM PHARM, 47(9), 1999, pp. 1297-1300
Citations number
16
Categorie Soggetti
Chemistry & Analysis
Journal title
CHEMICAL & PHARMACEUTICAL BULLETIN
ISSN journal
00092363 → ACNP
Volume
47
Issue
9
Year of publication
1999
Pages
1297 - 1300
Database
ISI
SICI code
0009-2363(199909)47:9<1297:SASOTM>2.0.ZU;2-Y
Abstract
Alkylation of 8-oxoadenosine (13) with 4-benzyloxy-3,5-dibromobenzyl bromid e (20), followed by Dimroth rearrangement and acid hydrolysis, provided N-( 3,5-dibromo-4-hydroxybenzyl)-8-oxoadenosine (15). The 2'-deoxy version of t his reaction sequence accomplished the first synthesis of N-(3,5-dibromo-4- hydroxybenzyl)-8-oxoadenine (16), which is the correct expression for marin e ascidian purine aplidiamine.