Total synthesis of antimalarial diterpenoid (+)-kalihinol A

Total synthesis of antimalarial diterpenoid (+)-kalihinol A

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 intramolec...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) Vol. 48; no. 6; p. 901
Main Authors: Miyaoka, Hiroaki, Abe, Yasunori, Sekiya, Nobuaki, Mitome, Hidemichi, Kawashima, Etsuko
Format: Journal Article
Language:English
Published: England 01-01-2012
Subjects:
Antimalarials - chemical synthesis
Diterpenes - chemical synthesis
Naphthalenes - chemistry
Stereoisomerism
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Summary: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.
ISSN:1364-548X
DOI:10.1039/c1cc16468f