Merck
CN

Total synthesis of (-)-isoavenaciolide.

The Journal of organic chemistry (2013-01-24)
David Santos, Xavier Ariza, Jordi Garcia, Paul Lloyd-Williams, Agustín Martínez-Laporta, Carolina Sánchez
ABSTRACT

An enantioselective approach to (-)-isoavenaciolide was achieved starting from 1-undecyn-3-ol. The synthesis relied upon the preparation of a chiral 4-silyloxy-2-alkenylborane by hydroboration of a protected 2,3-allenol and subsequent stereoselective addition to 2-thiophenecarboxaldehyde.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
γ-Butyrolactone, ReagentPlus®, ≥99%
Sigma-Aldrich
4-Hydroxybutanoic acid lactone, ≥98%, FCC, FG