Premium
Convergent Approaches to Saudin Intermediates
Author(s) -
Cravero Raquel M.,
GonzálezSierra Manuel,
Labadie Guillermo R.
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390223
Subject(s) - chemistry , steric effects , ketone , aldol condensation , aldol reaction , sesquiterpene , methyl vinyl ketone , fragmentation (computing) , alkyl , organic chemistry , catalysis , computer science , operating system
Different convergent approaches to the highly oxygenated sesquiterpene natural product saudin ( 1 ), has been investigated. Our strategy has included a Michael addition and aldol condensation reaction as key steps. During the synthetic development, we have found serious steric hindrance when an α ‐Me‐substituted alkyl vinyl ketone was used. Such steric hindrance has been overcome by synthesizing the vinyl ketone 16 through an anionic fragmentation, which was carefully studied. Finally, the intermediate 18 has been synthesized in a one‐pot reaction from the vinyl ketone 16 and has been cyclized to obtain the promising tricyclic intermediate 20 .