title: Biosynthetically inspired divergent approach to monoterpene indole alkaloids: total synthesis of mersicarpine, leuconodines B and D, leuconoxine, melodinine E, leuconolam, and rhazinilam.
abstract: Inspired by their potential biosynthesis, we have developed divergent total syntheses of seven monoterpene indole alkaloids including mersicarpine, leuconodines B and D, leuconoxine, melodinine E, leuconolam, and rhazinilam, and one unnatural analogue with an unprecedented structural skeleton. The key steps involve a Witkop-Winterfeldt oxidative indole cleavage followed by transannular cyclization. The transannular cyclization product was then converted to the corresponding structural skeletons by pairing its functional groups into different reaction modes.
authors.affiliation: Department of Chemistry and Center for Cancer Research, Purdue University, 720 Clinic Drive, West Lafayette, Indiana 47907, United States.
authors.forename: Yang
authors.initials: Y
authors.lastname: Yang
authors.affiliation: Department of Chemistry and Center for Cancer Research, Purdue University, 720 Clinic Drive, West Lafayette, Indiana 47907, United States.
authors.forename: Yu
authors.initials: Y
authors.lastname: Bai
authors.affiliation: Department of Chemistry and Center for Cancer Research, Purdue University, 720 Clinic Drive, West Lafayette, Indiana 47907, United States.
authors.forename: Siyuan
authors.initials: S
authors.lastname: Sun
authors.affiliation: Department of Chemistry and Center for Cancer Research, Purdue University, 720 Clinic Drive, West Lafayette, Indiana 47907, United States.
authors.forename: Mingji
authors.initials: M
authors.lastname: Dai
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D001381:Azepines / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D007212:Indolizines / Q000138:chemical synthesis / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D046948:Secologanin Tryptamine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001381:Azepines; D026121:Indole Alkaloids; D007212:Indolizines; D007769:Lactams; D046948:Secologanin Tryptamine Alkaloids; C000590191:leuconoxine; C529544:mersicarpine; C009170:rhazinilam; C062173:leuconolam