title: Synthesis of marine polycyclic polyethers via endo-selective epoxide-opening cascades.
abstract: The proposed biosynthetic pathways to ladder polyethers of polyketide origin and oxasqualenoids of terpenoid origin share a dramatic epoxide-opening cascade as a key step. Polycyclic structures generated in these biosynthetic pathways display biological effects ranging from potentially therapeutic properties to extreme lethality. Much of the structural complexity of ladder polyether and oxasqualenoid natural products can be traced to these hypothesized cascades. In this review we summarize how such epoxide-opening cascade reactions have been used in the synthesis of ladder polyethers and oxasqualenoid natural products.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA.
authors.forename: Ivan
authors.initials: I
authors.lastname: Vilotijevic
authors.forename: Timothy F
authors.initials: TF
authors.lastname: Jamison
mesh_terms: D000818:Animals; D001688:Biological Products / Q000097:blood / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D004852:Epoxy Compounds / Q000737:chemistry*; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D056890:Eukaryota / Q000737:chemistry; D008386:Marine Biology; D010944:Plants / Q000737:chemistry; D011161:Porifera / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D001688:Biological Products; D004852:Epoxy Compounds; D004987:Ethers; D011714:Pyrans
references.citation: J Am Chem Soc. 2008 Jun 11;130(23):7466-76
references.pmid: 18481856
references.citation: Chem Rev. 2005 Dec;105(12):4314-47
references.pmid: 16351046
references.citation: Angew Chem Int Ed Engl. 2006 Jul 3;45(27):4406-13
references.pmid: 16767782
references.citation: J Am Chem Soc. 2004 Nov 10;126(44):14374-6
references.pmid: 15521755
references.citation: Angew Chem Int Ed Engl. 1999 Jul 12;38(13-14):2012-2014
references.pmid: 34182660
references.citation: Toxicon. 2001 Jan;39(1):97-106
references.pmid: 10936626
references.citation: Org Lett. 2000 Sep 7;2(18):2917-9
references.pmid: 10964398
references.citation: J Antibiot (Tokyo). 1993 Mar;46(3):520-2
references.pmid: 8478272
references.citation: J Org Chem. 2009 Nov 6;74(21):8407-9
references.pmid: 19827774
references.citation: J Org Chem. 2003 Dec 26;68(26):10079-86
references.pmid: 14682703
references.citation: J Am Chem Soc. 1986 Nov 1;108(24):7855-6
references.pmid: 22283310
references.citation: Br J Cancer. 2004 Mar 8;90(5):1100-7
references.pmid: 14997213
references.citation: J Org Chem. 2005 Jan 21;70(2):721-4
references.pmid: 15651829
references.citation: J Am Chem Soc. 2009 May 13;131(18):6383-5
references.pmid: 19385615
references.citation: Tetrahedron. 2009 Aug 15;65(33):6648-6655
references.pmid: 20161178
references.citation: Org Lett. 2008 Aug 21;10(16):3465-8
references.pmid: 18646771
references.citation: Nature. 1998 Mar 19;392(6673):264-9
references.pmid: 9521320
references.citation: Angew Chem Int Ed Engl. 2006 Jan 23;45(5):810-2
references.pmid: 16355433
references.citation: J Ind Microbiol Biotechnol. 2003 Jul;30(7):383-406
references.pmid: 12898390
references.citation: Org Lett. 2009 Oct 1;11(19):4382-5
references.pmid: 19731936
references.citation: Org Lett. 2003 Jun 12;5(12):2123-6
references.pmid: 12790544
references.citation: Mar Biotechnol (NY). 2003 Jan-Feb;5(1):1-12
references.pmid: 12925913
references.citation: Org Lett. 2004 Nov 25;6(24):4487-9
references.pmid: 15548057
references.citation: Chem Soc Rev. 2009 Nov;38(11):3175-92
references.pmid: 19847350
references.citation: Nat Prod Rep. 2008 Apr;25(2):401-26
references.pmid: 18389143
references.citation: Chem Rev. 2008 Sep;108(9):3958-87
references.pmid: 18590339
references.citation: J Am Chem Soc. 2003 Jan 8;125(1):46-7
references.pmid: 12515504
references.citation: Chem Pharm Bull (Tokyo). 2001 May;49(5):613-8
references.pmid: 11383616
references.citation: J Org Chem. 1998 Sep 4;63(18):6200-6209
references.pmid: 11672250
references.citation: Science. 1993 Jan 22;259(5094):490-3
references.pmid: 8424171
references.citation: Mar Drugs. 2008 May 22;6(2):164-79
references.pmid: 18728765
references.citation: Science. 1997 Aug 15;277(5328):936-8
references.pmid: 9252321
references.citation: J Am Chem Soc. 2006 Feb 1;128(4):1056-7
references.pmid: 16433504
references.citation: Nat Prod Rep. 1995 Apr;12(2):165-81
references.pmid: 7739814
references.citation: Science. 2007 Aug 31;317(5842):1189-92
references.pmid: 17761875
references.citation: Eur J Biochem. 2000 Aug;267(16):5179-83
references.pmid: 10931202
references.citation: Nat Prod Rep. 2000 Jun;17(3):235-46
references.pmid: 10888011
references.citation: J Org Chem. 2002 Apr 19;67(8):2515-23
references.pmid: 11950296
references.citation: J Am Chem Soc. 2006 Aug 2;128(30):9648-50
references.pmid: 16866516
references.citation: J Am Chem Soc. 2009 May 20;131(19):6678-9
references.pmid: 19402635
references.citation: Cell Mol Neurobiol. 2004 Aug;24(4):553-63
references.pmid: 15233378
references.citation: Nat Prod Rep. 2009 Feb;26(2):266-80
references.pmid: 19177224
references.citation: J Am Chem Soc. 2007 Feb 7;129(5):1050-1
references.pmid: 17263384
references.citation: Mol Pharmacol. 1986 Aug;30(2):129-35
references.pmid: 2426567
references.citation: Phytochemistry. 2005 Aug;66(15):1767-80
references.pmid: 16051286
references.citation: Chembiochem. 2008 Dec 15;9(18):2967-75
references.pmid: 19025863
references.citation: J Org Chem. 2009 Feb 6;74(3):989-94
references.pmid: 19123836
references.citation: Chem Rev. 2005 Dec;105(12):4379-405
references.pmid: 16351048
references.citation: J Am Chem Soc. 2005 Apr 6;127(13):4586-7
references.pmid: 15796519
references.citation: Angew Chem Int Ed Engl. 2009;48(24):4430-2
references.pmid: 19431181
references.citation: Angew Chem Int Ed Engl. 2008;47(38):7182-225
references.pmid: 18763702
references.citation: J Am Chem Soc. 2009 Sep 2;131(34):12084-5
references.pmid: 19663441
references.citation: Am J Respir Crit Care Med. 2005 Jan 1;171(1):26-34
references.pmid: 15447946
references.citation: J Am Chem Soc. 2005 Apr 27;127(16):5806-7
references.pmid: 15839676
references.citation: Angew Chem Int Ed Engl. 2007;46(34):6481-4
references.pmid: 17668434
references.citation: Acc Chem Res. 2004 Aug;37(8):488-96
references.pmid: 15311947
references.citation: Toxicon. 1985;23(3):473-9
references.pmid: 3895583
references.citation: Angew Chem Int Ed Engl. 2008;47(23):4377-9
references.pmid: 18459096
references.citation: J Am Chem Soc. 2002 Dec 18;124(50):14983-92
references.pmid: 12475341
references.citation: J Am Chem Soc. 2007 Jun 27;129(25):7915-23
references.pmid: 17547399
references.citation: Nat Prod Rep. 2009 Jan;26(1):115-34
references.pmid: 19374125
references.citation: Org Lett. 2009 Aug 6;11(15):3490-2
references.pmid: 19588972
references.citation: Org Lett. 2002 Jul 25;4(15):2489-92
references.pmid: 12123358
references.citation: Toxicon. 2008 May;51(6):974-83
references.pmid: 18313714
references.citation: J Am Chem Soc. 2003 Oct 1;125(39):11893-9
references.pmid: 14505411
references.citation: Org Lett. 2003 Jun 26;5(13):2339-42
references.pmid: 12816443
references.citation: J Am Chem Soc. 2006 Dec 27;128(51):16989-99
references.pmid: 17177450
references.citation: Angew Chem Int Ed Engl. 2007;46(28):5278-82
references.pmid: 17469088
references.citation: Am J Physiol Cell Physiol. 2009 Dec;297(6):C1533-43
references.pmid: 19794142
references.citation: Chem Biol. 2006 Apr;13(4):453-60
references.pmid: 16632258
references.citation: Angew Chem Int Ed Engl. 2009;48(29):5250-81
references.pmid: 19572302
references.citation: Chem Res Toxicol. 2004 Sep;17(9):1251-7
references.pmid: 15377159
references.citation: J Am Chem Soc. 2003 Jul 2;125(26):7822-4
references.pmid: 12822999
references.citation: Science. 2009 Dec 18;326(5960):1662
references.pmid: 20019280
references.citation: Nature. 2005 Jun 9;435(7043):755-6
references.pmid: 15944690
references.citation: J Am Chem Soc. 2008 Sep 17;130(37):12230-1
references.pmid: 18710235
references.citation: Angew Chem Int Ed Engl. 2007;46(7):1132-5
references.pmid: 17191285