7,7-dimethyl-6,8-dioxabicyclo[3.3.0]oct-3-en-2-one as asynthetic equivalent of ketodicyclopentadiene: a new route to (-)-physostigmine, (-)-physovenine, and (-)-aphanorphine

Authors
Tanaka, K Taniguchi, T Ogasawara, K
Citation
K. Tanaka et al., 7,7-dimethyl-6,8-dioxabicyclo[3.3.0]oct-3-en-2-one as asynthetic equivalent of ketodicyclopentadiene: a new route to (-)-physostigmine, (-)-physovenine, and (-)-aphanorphine, TETRAHEDR L, 42(6), 2001, pp. 1049-1052
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
6
Year of publication
2001
Pages
1049 - 1052
Database
ISI
SICI code
0040-4039(20010205)42:6<1049:7AAE>2.0.ZU;2-A
Abstract
A new diastercocontrolled route to three alkaloids having a quaternary benz ylic stereogenic center, (-)-physostigmine, (-)-physovenine, and (-)-aphano rphine, has been developed using enantiopure 7,7-dimethyl-6,8-dioxabicyclo[ 3.3.0]oct-3-en-2-one as a synthetic equivalent of chiral cyclopentadienone. (C) 2001 Elsevier Science Ltd. All rights reserved.