Synthesis of polycyclic structures by Diels-Alder reaction using inner-outer-ring 1,3-bis[trimethylsilyloxy]dienes

Authors
Sestelo, JP Real, MD Mourino, A Sarandeses, LA
Citation
Jp. Sestelo et al., Synthesis of polycyclic structures by Diels-Alder reaction using inner-outer-ring 1,3-bis[trimethylsilyloxy]dienes, TETRAHEDR L, 40(5), 1999, pp. 985-988
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
5
Year of publication
1999
Pages
985 - 988
Database
ISI
SICI code
0040-4039(19990129)40:5<985:SOPSBD>2.0.ZU;2-S
Abstract
In this paper we describe regioselective one-pot preparations of inner-oute r-ring 1,3-bis[trimethylsilyloxy]dienes and their Diels-Alder reactions wit h electron-deficient dienophiles. The dienes were prepared in quantitative yield, and the Diels-Alder reactions proceeded smoothly, regioselectively a nd with good yields, allowing efficient construction of highly functionaliz ed polycyclic skeletons such as naphthofurans, benzofurans and various carb ocycles present in natural and non-natural products. (C) 1999 Elsevier Scie nce Ltd. All rights reserved.