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Total synthesis of antimalarial diterpenoid (+)-kalihinol A.

Chemical communications (Cambridge, England) (2011-12-06)
Hiroaki Miyaoka, Yasunori Abe, Nobuaki Sekiya, Hidemichi Mitome, Etsuko Kawashima
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Decahydronaphthalene, mixture of cis + trans, anhydrous, ≥99%
Sigma-Aldrich
trans-Decahydronaphthalene, 99%
Sigma-Aldrich
cis-Decahydronaphthalene, 99%
Sigma-Aldrich
Decahydronaphthalene, mixture of cis + trans, reagent grade, 98%