title: Stereospecific total synthesis of somocystinamide A.
abstract: The first total synthesis of somocystinamide A, a disulfide dimer with extremely labile enamide functional groups, was accomplished in a concise and stereospecific manner. Somocystinamide A is reported to possess exceptionally potent antiangiogenic and tumoricidal activities. The current work should enable further pharmacological investigation of this important natural product.
authors.affiliation: Scripps Institution of Oceanography and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California at San Diego, 9500 Gilman Drive, La Jolla, California 92093, USA.
authors.forename: Takashi L
authors.initials: TL
authors.lastname: Suyama
authors.forename: William H
authors.initials: WH
authors.lastname: Gerwick
mesh_terms: D000577:Amides / Q000737:chemistry; D001688:Biological Products / Q000737:chemistry; D004220:Disulfides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000577:Amides; D001688:Biological Products; D004220:Disulfides; C454639:Somocystinamide A
references.citation: Org Lett. 2004 May 27;6(11):1809-12
references.pmid: 15151420
references.citation: Org Lett. 2004 Feb 19;6(4):577-80
references.pmid: 14961627
references.citation: Planta Med. 1982 May;45(1):31-4
references.pmid: 7100305
references.citation: J Am Chem Soc. 2004 Jan 14;126(1):320-8
references.pmid: 14709098
references.citation: Nat Prod Rep. 2005 Oct;22(5):580-93
references.pmid: 16193157
references.citation: Org Lett. 2006 Sep 28;8(20):4541-3
references.pmid: 16986945
references.citation: Org Lett. 1999 Sep 23;1(6):953-6
references.pmid: 10823227
references.citation: Proc Natl Acad Sci U S A. 2008 Feb 19;105(7):2313-8
references.pmid: 18268346
references.citation: Alkaloids Chem Biol. 2001;57:75-184
references.pmid: 11705123
references.citation: Chemistry. 2001 Oct 1;7(19):4280-95
references.pmid: 11686609
references.citation: Org Lett. 2007 Dec 6;9(25):5267-70
references.pmid: 18001051
references.citation: Org Biomol Chem. 2005 Aug 7;3(15):2701-12
references.pmid: 16032348
references.citation: Org Biomol Chem. 2008 Apr 21;6(8):1478-97
references.pmid: 18385855
references.citation: Org Lett. 2004 Jan 8;6(1):27-30
references.pmid: 14703342
references.citation: J Nat Prod. 1999 Jun;62(6):934-6
references.pmid: 10395526
references.citation: Org Lett. 2002 Apr 4;4(7):1095-8
references.pmid: 11922791
references.citation: J Nat Prod. 2004 Aug;67(8):1356-67
references.pmid: 15332855
references.citation: Angew Chem Int Ed Engl. 2005 Jul 18;44(29):4490-527
references.pmid: 16003791
references.citation: Org Lett. 2003 Oct 2;5(20):3667-9
references.pmid: 14507200
references.citation: Chem Commun (Camb). 2005 Feb 28;(8):973-86
references.pmid: 15719090