A short synthetic route to nordihydroguaiaretic acid (NDGA) and its stereoisomer using Ti-induced carbonyl-coupling reaction

Authors
Gezginci, MH Timmermann, BN
Citation
Mh. Gezginci et Bn. Timmermann, A short synthetic route to nordihydroguaiaretic acid (NDGA) and its stereoisomer using Ti-induced carbonyl-coupling reaction, TETRAHEDR L, 42(35), 2001, pp. 6083-6085
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
35
Year of publication
2001
Pages
6083 - 6085
Database
ISI
SICI code
0040-4039(20010827)42:35<6083:ASSRTN>2.0.ZU;2-6
Abstract
A rapid synthetic approach to natural meso-nordihydroguaiaretic acid (NDGA) and its non-meso isomer is described from (3,4-dimethoxyphenyl)acetone usi ng as a key step the low-valent Ti-induced carbonyl-coupling reaction of th e ketone. The method involves a simple separation of the E- and Z-isomers t hat result from the dehydroxylation of the diol product of the coupling. Th e present approach allows the preparation of various analogs of NDGA. (C) 2 001 Elsevier Science Ltd. All rights reserved.