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Synlett 2010(17): 2589-2592
DOI: 10.1055/s-0030-1258574
DOI: 10.1055/s-0030-1258574
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Concise Total Synthesis of Vicenistatin
Further Information
Received
21 July 2010
Publication Date:
23 September 2010 (online)
Publication History
Publication Date:
23 September 2010 (online)
Abstract
A highly convergent total synthesis of macrocyclic lactam glycoside vicenistatin is described. Key features of the synthesis include rapid assembly of the macrolactam part and macrocyclic ring closure via intramolecular Stille coupling.
Key words
vicenistatin - macrolactam - vicenisamine - total synthesis
- Supporting Information for this article is available online:
- Supporting Information
- 1
Shindo K.Kamishohara M.Odagawa A.Matsuoka M.Kawai H. J. Antibiot. 1993, 46: 1076 - 2
Arai H.Matsushima Y.Eguchi T.Shindo K.Kakinuma K. Tetrahedron Lett. 1998, 39: 3181 -
3a
Matsushima Y.Itoh H.Eguchi T.Kakinuma K.
J. Antibiot. 1998, 51: 688 -
3b
Matsushima Y.Itoh H.Nakayama T.Horiuchi S.Eguchi T.Kakinuma K. J. Chem. Soc., Perkin Trans. 1 2002, 949 - 4
Matsushima Y.Nakayama T.Fujita M.Bhandari R.Eguchi T.Shindo K.Kakinuma K. J. Antibiot. 2001, 54: 211 - 5
Gassner NC.Tamble CM.Bock JE.Cotton N.White KN.Tenney K.St. Onge RP.Proctor MJ.Giaever G.Nislow C.Davis RW.Crews P.Holman TR.Lokey RS. J. Nat. Prod. 2007, 70: 383 - 6
Roush WR.Brown RJ. J. Org. Chem. 1983, 48: 5093 - 7
Martin SF.Dodge JA. Tetrahedron Lett. 1991, 32: 3017 - 8
Roush WR.James RA. Aust. J. Chem. 2002, 55: 141 -
9a
Nicolaou KC.Seitz SP.Papahatjis DP. J. Am. Chem. Soc. 1983, 105: 2430 -
9b
Nicolaou KC.Dolle RE.Papahatjis DP.Randall JL. J. Am. Chem. Soc. 1984, 106: 4189 - 10
Wipf P.Lim S. Angew. Chem., Int. Ed. Engl. 1993, 32: 1068 - 11
Dess DB.Martin JC. J. Org. Chem. 1983, 48: 4155 - 12
Brown HC.Bhat KS.Randad RS. J. Org. Chem. 1989, 54: 1570 - 13
Garber SB.Kingsbury JS.Gray BL.Hoveyda AH. J. Am. Chem. Soc. 2000, 122: 8168 - 14
Paquette LA.Duan MS.Konetzki I.Kempmann C.
J. Am. Chem. Soc. 2002, 124: 4257 - 15
Darwish A.Lang A.Kim T.Chong JM. Org. Lett. 2008, 10: 861 - 16
Schmidt JP.Beltran-Rodil S.Cox RJ.McAllister GD.Reid M.Taylor RJK. Org. Lett. 2007, 9: 4041 - 17
Nicolaou KC.Murphy F.Barluenga S.Ohshima T.Wei H.Xu J.Gray DLF.Baudoin O. J. Am. Chem. Soc. 2000, 122: 3830 - 18
Hashimoto S.Hayashi M.Noyori R. Tetrahedron Lett. 1984, 25: 1379 - 19
Mukaiyama T.Takashima T.Katsurada M.Aizawa H. Chem. Lett. 1991, 533