title: Synthesis of conjugated polyenes via sequential condensation of sulfonylphosphonates and aldehydes.
abstract: Selective metalation of sulfonylphosphonates results in sufficiently stable carbanions that undergo chemoselective Julia-Kocienski condensation with various aldehydes to provide (E)-allylic phosphonates in good yields and selectivities. The subsequent Horner-Wadsworth-Emmons condensation with aldehydes is used to synthesize various unsymmetrical trans-dienes, trienes, and tetraenes. This methodology is utilized for the concise synthesis of a naturally occurring fluorescent probe for membrane properties, β-parinaric acid.
authors.affiliation: Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
authors.forename: Nathan R
authors.initials: NR
authors.lastname: Cichowicz
authors.forename: Pavel
authors.initials: P
authors.lastname: Nagorny