A carbonyl oxide route to antimalarial yingzhaosu A analogues: Synthesis and antimalarial activity

Ozonolysis of R-carvone and in situ trapping with primary alcohols ROH (R= Me, Et, Bu, Pent, Oct) produces hydroperoxy ketals (5a-e) as a 1:1 mixture of diastereomers. Cyclisation of these intermediates with catalytic sodium methoxide in methanol produces the corresponding endoperoxide derivatives (...

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Published inTetrahedron letters Vol. 39; no. 33; pp. 6065 - 6068
Main Authors O' Neill, Paul M, Searle, Natalie L, Raynes, Kaylene J, Maggs, James L, Ward, Stephen A, Storr, Richard C, Park, B.Kevin, Posner, Gary H
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 13.08.1998
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:Ozonolysis of R-carvone and in situ trapping with primary alcohols ROH (R= Me, Et, Bu, Pent, Oct) produces hydroperoxy ketals (5a-e) as a 1:1 mixture of diastereomers. Cyclisation of these intermediates with catalytic sodium methoxide in methanol produces the corresponding endoperoxide derivatives (6a-6e). The pentyl and octyl endoperoxide derivatives demonstrate reasonable antimalarial potency in vitro against the HB3 strain of Plasmodium falciparum. A mechanism for antimalarial action involving the formation of a C-centred radical is proposed. Ozonolysis of R-carvone in the presence of various alcohols produces the peroxy scelatls 5a-5e which can be cyclised to the enantoopure endoperoxides 6a-6e
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)01248-9