First total synthesis of cassiarin A, a naturally occurring potent antiplasmodial alkaloid

Organic Letters

Volumn 10, Issue 10, 2008, Pages 1921-1922

  Rudyanto, Marcellino ^b   Tomizawa, Yuichiro ^b   Morita, Hiroshi ^b   Honda, Toshio ^a,b  

^a HOSHI UNIVERSITY   (Japan)

^b AIRLANGGA UNIVERSITY   (Indonesia)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ANTIMALARIAL AGENT; CASSIARIN A; FUSED HETEROCYCLIC RINGS;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SENNA; SYNTHESIS;

ALKALOIDS; ANTIMALARIALS; CASSIA; HETEROCYCLIC COMPOUNDS, 3-RING; MOLECULAR STRUCTURE;

EID: 44949135217     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8004112     Document Type: Article

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22. Attempted conversion of cassiarin A to cassiarin B by direct alkylation with methyl bromo- or iodobutyrate under various reaction conditions failed, unfortunately. Similar akylation of O-Bn or O-MOM cassiarin A did not give corresponding quaternary salts. When cassiarin A was treated with methyl bromobutyrate in the presence of a base, O-alkylated compound was isolated as the sole product.