Toward tubulysin: gram-scale synthesis of tubuvaline-tubuphenylalanine fragment.
A practical and stereoselective synthesis of the tubuvaline-tubuphenylalanine (Tuv-Tup) fragment of tubulysin is achieved involving the opening of aziridine, crucial MacMillan alpha-hydroxylation on both fragments, and an epoxide-opening reaction.
Chandrasekhar
Srivari
S
Organic Division-I, Indian Institute of Chemical Technology, Hyderabad 500 607, India. srivaric@iict.res.in
Mahipal
Bodugam
B
Kavitha
Mitta
M
D000080462:Acyclic Monoterpenes; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D006900:Hydroxylation; D039821:Monoterpenes / Q000737:chemistry; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D010446:Peptide Fragments / Q000138:chemical synthesis* / Q000737:chemistry; D010649:Phenylalanine / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D014633:Valine / Q000138:chemical synthesis / Q000737:chemistry*
D000080462:Acyclic Monoterpenes; D000970:Antineoplastic Agents; D001388:Aziridines; D004852:Epoxy Compounds; D039821:Monoterpenes; D009842:Oligopeptides; D010446:Peptide Fragments; C502386:tubulysin D; D010649:Phenylalanine; C033132:aziridine; D014633:Valine; C007078:citronellol