title: Concise total synthesis of (+/-)-pseudotabersonine via double ring-closing metathesis strategy.
abstract: A concise synthesis of (+/-)-pseudotabersonine from commercially available 1-(phenylsulfonyl)-3-indolecarboxaldehyde has been accomplished. This synthesis features the convergent assembly of a key intermediate via a stepwise variant of a Mannich-type multicomponent coupling process, a double ring-closing metathesis, and a one-pot deprotection/cyclization reaction.
authors: Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712, USA.
authors: Bo
authors: B
authors: Cheng
authors: James D
authors: JD
authors: Sunderhaus
authors: Stephen F
authors: SF
authors: Martin
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D029062:Apocynaceae / Q000737:chemistry; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C553349:1-(phenylsulfonyl)-3-indolecarboxaldehyde; D000447:Aldehydes; D026121:Indole Alkaloids; D007211:Indoles; C553348:pseudotabersonine