A novel synthetic approach to benzo[h]chromones via sequential intramolecular alkynoyl transfer followed by 6-endo ring closure

Authors
Sakamoto, K Honda, E Ono, N Uno, H
Citation
K. Sakamoto et al., A novel synthetic approach to benzo[h]chromones via sequential intramolecular alkynoyl transfer followed by 6-endo ring closure, TETRAHEDR L, 41(11), 2000, pp. 1819-1823
Citations number
13
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
11
Year of publication
2000
Pages
1819 - 1823
Database
ISI
SICI code
0040-4039(20000311)41:11<1819:ANSATB>2.0.ZU;2-Y
Abstract
An intramolecular acyl transfer reaction took place on treatment of 1-metho xymethoxy-3-(2-alkynoyloxy)methyl-2-iodonaphthalenes with n-BuLi at -78 deg rees C to give 1-methoxymethoxy-2-alkynoyl-3-hydroxymethylnaphthalenes in h igh yields. After protection of the hydroxymethyl group as benzoates, forma tion of a phi-pyrone ring was easily achieved by deprotection of the MOM gr oup followed by spontaneous 6-endo-digonal ring closure under mild acidic c onditions. (C) 2000 Elsevier Science Ltd. All rights reserved.