title: Syntheses and cytotoxicity of (R)- and (S)-7-methoxycryptopleurine.
abstract: 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.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante , Apdo. 99, 03080 Alicante, Spain.
authors.forename: Cintia
authors.initials: C
authors.lastname: Anton-Torrecillas
authors.forename: Irene
authors.initials: I
authors.lastname: Bosque
authors.forename: Jose C
authors.initials: JC
authors.lastname: Gonzalez-Gomez
authors.forename: María Isabel
authors.initials: MI
authors.lastname: Loza
authors.forename: José
authors.initials: J
authors.lastname: Brea
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D045744:Cell Line, Tumor; D006801:Humans; D015394:Molecular Structure; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C518787:7-methoxycryptopleurine; D000970:Antineoplastic Agents; D011807:Quinolizines; D012238:Rhodium