First Total Synthesis of (±)-Prelunularin

Abstract

The first total synthesis of (±)-prelunularin is described employing an intramolecular aldol addition/sulfinate elimination tandem reaction. Investigations on the mechanism of the one-pot cyclization reaction using time-dependent NMR spectroscopy suggested that the sulfinate elimination took place before the intramolecular ring-closing aldol addition.

Unexpected Steric Effects of “Remote” Alkyl Groups on the Rate of Conjugate Additions to Alkyl α,β-Ethylenic Sulfones, Sulfoxides, and Esters

“…The ethyl vinyl sulfoxide ( 2a ) and tert -butyl vinyl sulfoxide ( 2b ) were prepared according to Jenks . Ethyl 4-phenyl-2( E )-pentenoate ( 3a ) and tert -butyl 4-phenyl-2( E )-pentenoate ( 3c ) were synthesized according to a procedure by Pandolfi . The compounds 2a , 2c , 3a , and 3c are all known, and their structures are consistent with their published data.…”

Asymmetric synthesis of a model compound for the cyclohexenone core of ambuic acid

“…We are currently investigating the total synthesis of ambuic acid using sulphonylcarbanion chemistry for the introduction of the hydroxymethylene group on carbon 8. 20 We are also attempting the synthesis of other natural epoxyenones 6 such as bromoxone and parasitenone.…”