Syntheses and Cytotoxicity of (R)- and (S)‑7-Methoxycryptopleurine

Two efficient protocols are described for the transformation of a key chiral homoallyllic sulfinamine intermediate in four steps into enantioenriched 7-methoxycryptopleurine. While one of the protocols relied on a rhodium catalyzed linear hydroformylation process, the alternative approach was based...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-01, Vol.80 (2), p.1284-1290
Main Authors: Anton-Torrecillas, Cintia, Bosque, Irene, Gonzalez-Gomez, Jose C, Loza, María Isabel, Brea, José
Format: Article
Language:English
Subjects:
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - toxicity
Cell Line, Tumor
Humans
Molecular Structure
Quinolizines - chemical synthesis
Quinolizines - chemistry
Rhodium - chemistry
Stereoisomerism
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Summary:Two efficient protocols are described for the transformation of a key chiral homoallyllic sulfinamine intermediate in four steps into enantioenriched 7-methoxycryptopleurine. While one of the protocols relied on a rhodium catalyzed linear hydroformylation process, the alternative approach was based on a ring-closing metathesis from the corresponding N-allyl-sulfinamine. The cytotoxic evaluation of both enantiomers of the target compound demonstrated that the (R)-compound is much more potent than its antipode against the four cancer cell lines examined.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo502660r