title: Stereoselective total synthesis of (+)-oploxyne A, (-)-oploxyne B, and their C-10 epimers and structure revision of natural oploxyne B.
abstract: The first total synthesis of recently isolated diacetylene alcohols oploxyne A, oploxyne B, and their C-10 epimers was accomplished. The structure of natural oploxyne B has been revised. The key steps involved are base-induced double elimination of a carbohydrate-derived β-alkoxy chloride to generate the chiral acetylenic alcohol and Cadiot-Chodkiewicz cross-coupling reaction. The target compounds displayed potent cytotoxicity against neuroblastoma and prostate cancer cell lines.
authors.affiliation: Organic Division-I, Indian Institute of Chemical Technology, CSIR, Hyderabad-500 607, India. yadavpub@iict.res.in
authors.forename: J S
authors.initials: JS
authors.lastname: Yadav
authors.forename: Kumaraswamy
authors.initials: K
authors.lastname: Boyapelly
authors.forename: Sathish Reddy
authors.initials: SR
authors.lastname: Alugubelli
authors.forename: Srihari
authors.initials: S
authors.lastname: Pabbaraja
authors.forename: Janakiram R
authors.initials: JR
authors.lastname: Vangala
authors.forename: Shasi V
authors.initials: SV
authors.lastname: Kalivendi
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000627:therapeutic use; D001943:Breast Neoplasms / Q000188:drug therapy / Q000473:pathology; D002384:Catalysis; D045744:Cell Line, Tumor; D004317:Doxorubicin / Q000494:pharmacology; D005260:Female; D006801:Humans; D008175:Lung Neoplasms / Q000188:drug therapy / Q000473:pathology; D008297:Male; D015394:Molecular Structure; D009447:Neuroblastoma / Q000188:drug therapy / Q000473:pathology; D053279:Polyynes / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000627:therapeutic use; D011471:Prostatic Neoplasms / Q000188:drug therapy / Q000473:pathology; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; C550046:oploxyne B; D053279:Polyynes; D004317:Doxorubicin