Total synthesis of antimalarial diterpenoid (+)-kalihinol A
Hiroaki Miyaoka1, Yasunori Abe, Nobuaki Sekiya
1School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan. miyaokah@toyaku.ac.jp
Chemical Communications (Cambridge, England)
|December 6, 2011
Abstract:
Total synthesis of antimalarial diterpenoid (+)-kalihinol A, isolated from marine sponge Acanthella sp., is achieved. This total synthesis involves regioselective alkylation of an epoxide, construction of a tetrahydropyran ring by iodo-etherification, construction of a cis-decalin ring by intramolecular Diels-Alder reaction, isomerization of cis-decalin to trans-decalin, and subsequent functionalization of the trans-decalin ring.
