2013 年 71 巻 6 号 p. 637-638
Aplyviolene (1) is a diterpene isolated from marine sponge, it has characteristic structures of cis-perhydroazulene and 6-acetoxy-2,7-dioxabicyclo[3.2.1]-octan-3-one moieties. One of the synthetic challenges of 1 is a stereoselective construction of continuous carbon centers at C8 (quaternary carbon) and C14. In this mini review, a total synthesis of aplyviolene by Overman was discussed focusing on the control of those stereocenters by using prochiral nucleophiles of 6 or 10 with electrophiles.