1993 年 51 巻 12 号 p. 1164-1177
Synthetic studies on the clerodane diterpenoids, a rapidly growing group of natural products, are reviewed from the standpoint of stereocontrols for the construction of a unique four contiguous stereogenic centers on their bicyclic skeleton. Strategies for the clearance of the stereochemical problems are described according to the types of major stereochemical features-namely trans and cis with respects to the ring fusion, and cis and trans disposition of C1-unit at C-8 and C-9 positions. The description involves the methods for enantioselective synthesis. Brief mentions are made on the synthetic methods for the related natural products (sesqui-, di- and sesterditerpenoids) with “clerodane” skeleton or substitution (hence with common problems of the stereocontrol) and on the investigations for the construction of the specific groupings in bioactive clerodane diterpenoids. The preliminary approaches as well as the methods used in the successful total synthesis are introduced in the modern light of stereocontrols.