RAPID ACCESS TO TRICYCLIC COMPOUNDS USING ZIRCONIUM CHEMISTRY AND INTRAMOLECULAR DIELS-ALDER REACTIONS - SYNTHESIS OF THE PISIFERANOL AND DOLASTANE SKELETONS

Authors
TUCKETT MW WATKINS WJ WHITBY RJ
Citation
Mw. Tuckett et al., RAPID ACCESS TO TRICYCLIC COMPOUNDS USING ZIRCONIUM CHEMISTRY AND INTRAMOLECULAR DIELS-ALDER REACTIONS - SYNTHESIS OF THE PISIFERANOL AND DOLASTANE SKELETONS, Tetrahedron letters, 39(1-2), 1998, pp. 123-126
Citations number
39
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
1-2
Year of publication
1998
Pages
123 - 126
Database
ISI
SICI code
0040-4039(1998)39:1-2<123:RATTCU>2.0.ZU;2-0
Abstract
Zirconium mediated cocyclisation of alpha,omega-dienes to give zircona bicycles, followed by allylcarbenoid insertion, electrophile addition, and iodine quench gave highly functionalised organic structures. Furt her elaboration including an intramolecular Diels-Alder reaction gave a variety of fused tricyclic compounds including the 5,7,6 skeleton of the dolastane diterpenes and the 6,7,6 (aromatic) rearranged 9(10-->1 20)-abeo-abietane skeleton of pisiferanol. (C) 1997 Elsevier Science L td. All rights reserved.