First Synthesis of All-trans-polyprenol with 100 Carbons

All-trans polyprenols consisting of one hundred carbons (C100) have been synthesized for the first time via the sulfone coupling of C45 and C55 fragments. The resulting coupling product with four benzenesulfonyl groups were subjected to desulfonylation reaction using Pd(dppp)Cl2/LiBHEt3 followed by removal of the benzyl group at the tail under Benkeser reduction conditions to furnish the title compound. An all-trans polyprenol consisting of one hundred carbons (C100) has been synthesized for the first time by the sulfone coupling of C45 and C55 fragments.