合成路线1

alpha-D-Glucoheptonic acid gamma-lactone (I) was protected as the bis(acetonide) (II) upon treatment with a catalytic amount of I2 in acetone. The free hydroxyl group of (II) was then alkylated with iodomethane in the presence of silver oxide, yielding the methyl ether (III). Selective hydrolysis of the 1,2-acetonide of (III) was accomplished by treatment of the bis(acetonide) (III) with aqueous acetic acid. Oxidative cleavage of the resultant vicinal diol (IV) using NaIO4 gave aldehyde (V). Then, olefination of aldehyde (V) with the low-valent organochromium species generated in situ from 1,1-diiodoneopentane (VI) and CrCl2 produced the target E-olefin (VII) as the major isomer.