SYNTHESIS OF OCTAHYDROBENZO[B]FURANS USING TANDEM CONJUGATE ADDITION-REACTIONS INITIATED BY OXYGEN NUCLEOPHILE

Authors
YAKURA T YAMADA S SHIMA M IWAMOTO M IKEDA M
Citation
T. Yakura et al., SYNTHESIS OF OCTAHYDROBENZO[B]FURANS USING TANDEM CONJUGATE ADDITION-REACTIONS INITIATED BY OXYGEN NUCLEOPHILE, Chemical and Pharmaceutical Bulletin, 46(5), 1998, pp. 744-748
Citations number
35
Categorie Soggetti
Chemistry Medicinal",Chemistry,"Pharmacology & Pharmacy
Journal title
Chemical and Pharmaceutical Bulletin → ACNP
ISSN journal
00092363
Volume
46
Issue
5
Year of publication
1998
Pages
744 - 748
Database
ISI
SICI code
0009-2363(1998)46:5<744:SOOUTC>2.0.ZU;2-T
Abstract
When 1-nitrocyclohexene (1) was treated with methyl 4-hydroxy-2-butyno ate (2) in the presence of potassium tert-butoxide in tetrahydrofuran- tert-butanol at 0 degrees C for 10 min, a tandem conjugate addition pr oduct, methyl nitrooctahydrobenzo[b]furan-Delta(3,alpha)-acetate (3a), was obtained in quantitative yield as a 55:45 mixture of the (Z)- and (E)-isomers. The scope and limitations of this reaction were examined . Some transformation reactions of 3a are also described.