title: Synthesis of D-abrines by palladium-catalyzed reaction of ortho-iodoanilines with N-Boc-N-methylalanyl-substituted acetaldehyde and acetylene.
abstract: A novel strategy to N-Boc-N-methyl--tryptophans (abrine derivatives) was developed that relies on the palladium-catalyzed annulation of ortho-iodoanilines 12 with either N-Boc-N-methyl-propargylglycine 16 or aldehyde 11. Both 11 and 16 can be prepared from d-serine. An alternative route to propargylglycine 16 utilizes an enantioselective propargylation reaction of glycine imine 17.
authors: Institut für Organische Chemie, Universität Tübingen , Auf der Morgenstelle 18, 72076 Tübingen, Germany.
authors: Paulami
authors: P
authors: Danner
authors: Marius
authors: M
authors: Morkunas
authors: Martin E
authors: ME
authors: Maier
mesh_terms: D000079:Acetaldehyde / Q000737:chemistry*; D000114:Acetylene / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry*; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000737:chemistry*
chemical_list: D000814:Aniline Compounds; D026121:Indole Alkaloids; D010165:Palladium; D014364:Tryptophan; D000079:Acetaldehyde; D000114:Acetylene; C496492:abrine
references: J Antibiot (Tokyo). 1995 Nov;48(11):1262-6
references: 8557566
references: Org Lett. 2005 Sep 15;7(19):4111-2
references: 16146364
references: Org Lett. 2004 Sep 16;6(19):3217-9
references: 15355016
references: Org Lett. 2002 Nov 28;4(24):4245-8
references: 12443069
references: Org Lett. 2010 Mar 5;12(5):1040-3
references: 20141170
references: Chem Rev. 2004 Dec;104(12):5823-46
references: 15584690
references: J Org Chem. 2009 Nov 6;74(21):8425-7
references: 19821609
references: Org Lett. 2012 Jan 6;14(1):150-3
references: 22149572
references: J Org Chem. 2003 Apr 4;68(7):2652-67
references: 12662035
references: J Am Chem Soc. 2009 May 13;131(18):6360-1
references: 19374357
references: Chem Rev. 2011 May 11;111(5):PR215-83
references: 21557620
references: Bioorg Med Chem Lett. 2009 Aug 1;19(15):4427-31
references: 19523824
references: J Org Chem. 2006 Sep 29;71(20):7826-34
references: 16995692
references: J Org Chem. 2002 Sep 20;67(19):6841-4
references: 12227823
references: J Am Chem Soc. 2008 Oct 15;130(41):13538-9
references: 18800798
references: Org Biomol Chem. 2003 Mar 21;1(6):973-7
references: 12929636
references: J Org Chem. 1997 May 2;62(9):2676-2677
references: 11671622
references: J Am Chem Soc. 2010 Mar 10;132(9):3063-77
references: 20148556