Synthesis of (35)- and (3R)-3-Hydroxy-p-ionone and Their Transformation into (35)- and (3H)-beta-Cryptoxanthin

摘要

(3R)-3-Hydroxy-bea-ionone and (3S)-3-hydroxy-beta-ionone were synthesized in high enantiomeric purity from commercially available (+-)-alpha-ionone. These ionones were then transformed into (3R)-beta-cryptoxanthin and (3S)-beta-cryptoxanthin by a C_(15)+C_(10)+C_(15) Wittig coupling strategy according to known methods. This methodology can considerably simplify the total synthesis of optically active carotenoids with 3-hydroxy-beta-end groups that possess significant biological activities.