Regiospecific substitution of the carbon-boron bond of tris(4-methylfuran-3-yl)boroxine: a model ring C -> BC -> ABC approach towards eudesmanolides

Authors
Yick, CY Wong, HNC
Citation
Cy. Yick et Hnc. Wong, Regiospecific substitution of the carbon-boron bond of tris(4-methylfuran-3-yl)boroxine: a model ring C -> BC -> ABC approach towards eudesmanolides, TETRAHEDRON, 57(32), 2001, pp. 6935-6940
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
32
Year of publication
2001
Pages
6935 - 6940
Database
ISI
SICI code
0040-4020(20010806)57:32<6935:RSOTCB>2.0.ZU;2-P
Abstract
A synthetic study of eudesmanolides was performed utilizing a Suzuki coupli ng reaction of tris(4-methylfuran-3-yl)boroxine (6) as the pivotal step. Th e other key reactions involved Friedel-Crafts acylation, Wacker-Tsuji react ion and aldol condensation. In this Ring C-BC-ABC approach, a model compoun d 3 towards the synthesis of eudesmanolides 11,13-dihydrotubiferin (1) and artogallin (2) was realized. In another model study, the five-membered anal og 4 was also obtained. (C) 2001 Elsevier Science Ltd. All rights reserved.