title: Synthesis of the bis-tetrahydropyran core of amphidinol 3.
abstract: A convergent synthesis of the C31-C52 bis-tetrahydropyran core of the natural product amphidinol 3 is reported. A common intermediate was synthesized from d-tartaric acid utilizing an asymmetric glycolate alkylation/ring-closing metathesis sequence to construct the THP rings. Differential elaboration of the common intermediate allowed the synthesis of two distinct coupling partners which were joined through a modified Horner-Wadsworth-Emmons olefination to provide the bis-tetrahydropyran core.
authors.affiliation: Kenan and Caudill Laboratories of Chemistry, University of North Carolina at Chapel Hill, North Carolina 27599, USA. crimmins@email.unc.edu
authors.forename: Michael T
authors.initials: MT
authors.lastname: Crimmins
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Martin
authors.forename: Theodore A
authors.initials: TA
authors.lastname: Martinot
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D004141:Dinoflagellida / Q000737:chemistry; D008387:Marine Toxins / Q000138:chemical synthesis; D015394:Molecular Structure; D035964:Oxocins / Q000138:chemical synthesis; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013644:Tartrates / Q000737:chemistry; D000095722:Amphidinols
chemical_list: D000475:Alkenes; D001688:Biological Products; D008387:Marine Toxins; D035964:Oxocins; D011714:Pyrans; D013644:Tartrates; C438973:amphidinol 3; D000095722:Amphidinols; C029768:tartaric acid
references.citation: Angew Chem Int Ed Engl. 1998 Aug 17;37(15):1986-2012
references.pmid: 29711061
references.citation: Org Lett. 2005 Jul 7;7(14):3111-4
references.pmid: 15987218
references.citation: Org Lett. 2008 Feb 21;10(4):681-4
references.pmid: 18205377
references.citation: Org Lett. 2003 Feb 20;5(4):591-4
references.pmid: 12583777
references.citation: Org Lett. 2001 May 17;3(10):1451-4
references.pmid: 11388839
references.citation: Org Lett. 2005 Apr 28;7(9):1853-6
references.pmid: 15844923
references.citation: Org Lett. 1999 Dec 16;1(12):2029-32
references.pmid: 10836060
references.citation: Org Lett. 2007 Feb 1;9(3):513-6
references.pmid: 17249800
references.citation: Org Lett. 2007 Nov 8;9(23):4757-60
references.pmid: 17944478
references.citation: Angew Chem Int Ed Engl. 2006 Mar 13;45(12):1900-3
references.pmid: 16470898
references.citation: J Org Chem. 2009 Nov 20;74(22):8810-3
references.pmid: 19852459
references.citation: Nat Protoc. 2007;2(10):2451-8
references.pmid: 17947986
references.citation: Angew Chem Int Ed Engl. 2006 Nov 6;45(43):7258-62
references.pmid: 17013953
references.citation: Org Lett. 2005 Nov 24;7(24):5509-12
references.pmid: 16288543
references.citation: Org Lett. 2008 Nov 20;10(22):5203-6
references.pmid: 18959425
references.citation: Org Lett. 2005 Mar 31;7(7):1411-4
references.pmid: 15787519