Synthetic studies towards (+)-Dihydroampullicin. Michael addition of N-Boc-2-(tert-butyldimethylsiloxy)-3-methyl-pyrrole to alpha-methylene lactones

Authors
Marcos, I Redero, E Bermejo, F
Citation
I. Marcos et al., Synthetic studies towards (+)-Dihydroampullicin. Michael addition of N-Boc-2-(tert-butyldimethylsiloxy)-3-methyl-pyrrole to alpha-methylene lactones, TETRAHEDR L, 41(44), 2000, pp. 8451-8455
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
44
Year of publication
2000
Pages
8451 - 8455
Database
ISI
SICI code
0040-4039(20001028)41:44<8451:SST(MA>2.0.ZU;2-X
Abstract
The Michael addition of N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy )-3-methyl-pyrrole (4) to several alpha -methylene lactones catalyzed by fl uoride ions yielded the corresponding homologated products (26-30) with goo d yields. Application of this reaction to the sililoxy bicyclic lactone (5) allowed us to isolate the tricyclic lactone (26), a highly valuable interm ediate in our synthetic strategy leading to the growth regulator (+)-Dihydr oampullicin (1). (C) 2000 Elsevier Science Ltd. All rights reserved.