Concise total synthesis of (+/-)-pseudotabersonine via double ring-closing metathesis strategy.
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.
Cheng
Bo
B
Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712, USA.
Sunderhaus
James D
JD
Martin
Stephen F
SF
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
C553349:1-(phenylsulfonyl)-3-indolecarboxaldehyde; D000447:Aldehydes; D026121:Indole Alkaloids; D007211:Indoles; C553348:pseudotabersonine