Revised structure of gonioheptolide A

Authors
Mukai, C Yamashita, H Hirai, S Hanaoka, M McLaughlin, JL
Citation
C. Mukai et al., Revised structure of gonioheptolide A, CHEM PHARM, 47(1), 1999, pp. 131-132
Citations number
11
Categorie Soggetti
Chemistry & Analysis
Journal title
CHEMICAL & PHARMACEUTICAL BULLETIN
ISSN journal
00092363 → ACNP
Volume
47
Issue
1
Year of publication
1999
Pages
131 - 132
Database
ISI
SICI code
0009-2363(199901)47:1<131:RSOGA>2.0.ZU;2-9
Abstract
(+/-)-Gonioheptolide A (3) was unambiguously synthesized from (+/-)-goniofu pyrone (4) and thereby its structure was revised as (1'R*,2S*,3S*,4S*,5R*)- 3,4-dihydroxy-2-[(1'-hydroxy-2'-methoxycarbonyl)ethyl]-5-phenyltetrahydrofu ran. Methanolysis of (+/-)-goniofupyrone (4) with conc.H2SO4 at room temper ature provided (+/-)-gonioheptolide A (3) in 48% yield. The synthetic (+/-) -gonioheptolide A and its triacetate were comparable to natural gonioheptol ide A and its triacetate, respectively.