title: Synthesis of Bisindole Alkaloids from the Apocynaceae Which Contain a Macroline or Sarpagine Unit: A Review.
abstract: Bisindole natural products consist of two monomeric indole alkaloid units as their obligate constituents. Bisindoles are more potent with respect to their biological activity than their corresponding monomeric units. In addition, the synthesis of bisindoles are far more challenging than the synthesis of monomeric indole alkaloids. Herein is reviewed the enantiospecific total and partial synthesis of bisindole alkaloids isolated primarily from theAlstoniagenus of theApocynaceaefamily. The monomeric units belong to the sarpagine, ajmaline, macroline, vobasine, and pleiocarpamine series. An up-to-date discussion of their isolation, characterization, biological activity as well as approaches to their partial and total synthesis by means of both synthetic and biosynthetic strategies are presented.
authors.affiliation: Department of Chemistry and Biochemistry, University of Wisconsin-Milwaukee, 3210 N. Cramer Street, Milwaukee, WI 53201, USA. mdrahman@uwm.edu.
authors.forename: Md Toufiqur
authors.initials: MT
authors.lastname: Rahman
authors.affiliation: Department of Chemistry and Biochemistry, University of Wisconsin-Milwaukee, 3210 N. Cramer Street, Milwaukee, WI 53201, USA. tiruvee2@uwm.edu.
authors.forename: Veera V N Phani Babu
authors.initials: VV
authors.lastname: Tiruveedhula
authors.affiliation: Department of Chemistry and Biochemistry, University of Wisconsin-Milwaukee, 3210 N. Cramer Street, Milwaukee, WI 53201, USA. capncook@uwm.edu.
authors.forename: James M
authors.initials: JM
authors.lastname: Cook
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D029062:Apocynaceae / Q000737:chemistry*; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D000078183:Oxindoles; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013237:Stereoisomerism; D014747:Vinblastine / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D014750:Vincristine / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D026121:Indole Alkaloids; D000078183:Oxindoles; D010936:Plant Extracts; C512190:macroline; D014750:Vincristine; D014747:Vinblastine; C475809:sarpagine
keywords: Alstonia genus; Apocynaceae family; ajmaline; bioactive indole alkaloids; biomimetic synthesis; bisindole alkaloids; enantiospecific and regiospecific synthesis of alkaloids; macroline; partial and total synthesis; sarpagine