New route to the synthesis of the illudane skeleton by Michael-Michael-elimination reaction

Authors
Tokuzaki, K Kanemitu, Y Yoshimitsu, T Nagaoka, H
Citation
K. Tokuzaki et al., New route to the synthesis of the illudane skeleton by Michael-Michael-elimination reaction, TETRAHEDR L, 41(31), 2000, pp. 5923-5926
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
31
Year of publication
2000
Pages
5923 - 5926
Database
ISI
SICI code
0040-4039(20000729)41:31<5923:NRTTSO>2.0.ZU;2-C
Abstract
A new route to the synthesis of an optically active illudane skeleton from (R)-(-)-pantolactone (4) is established. The tricyclic ring system was cons tructed by Michael-Michael-elimination reaction of the enolate of (3S,5R)-3 -(tert-butyldimethylsilyloxy)-5-methoxymethyloxy-1-propionylcyclopentene (1 0) with ethyl cyclopropylidenacetate (3). (C) 2000 Elsevier Science Ltd. Al l rights reserved.