Abstract
Zincophorin C1-C9 fragment and seven tetrahydropyran analogues
were prepared diastereoselectively by sequential iodoetherification
and radical hydrogen-transfer reactions. Stereoselective formation
of 3,7-trans or 3,7-cis rings
was rationalized through minimization of allylic-1,3 strain in chair-like
transition states. Subsequent hydrogen-transfer provided 7,8-anti or 7,8-syn isomers
under acyclic stereocontrol or endocyclic control respectively.
The latter approach relies on the formation of a [4.4.0] bicyclic
complexes resulting from the chelation of the oxygen of the tetrahydropyran
ring and the ester by a bidentate Lewis acid.
Key words
ionophore - iodoetherification - radical reduction - Lewis acid - substituted tetrahydropyrans
References
1a Song ZL.
Lohse AG.
Hsung RP.
Nat. Prod. Rep.
2009,
26:
560
1b Harrison TJ.
Ho S.
Leighton JL.
J. Am. Chem. Soc.
2011,
133:
7308
1c Mochirian P.
Godin F.
Katsoulis I.
Fontaine I.
Brazeau J.-F.
Guindon Y.
J. Org. Chem.
2011,
76:
7654
2 Faul MM.
Huff BE.
Chem. Rev.
2000,
100:
2407
3a Beug H.
Cell
2009,
138:
623
3b Gupta PB.
Onder TT.
Jiang GZ.
Tao K.
Kuperwasser C.
Weinberg RA.
Lander ES.
Cell
2009,
138:
645
4 Sippl W. In Pharmacophores and Pharmacophore Searches
Langer T.
Hoffmann RD.
Wiley-VCH;
Weinheim:
2006.
p.395
5a Brooks HA.
Gardner D.
Poyser JP.
King TJ.
5b Gräfe U.
Schade W.
Roth M.
Radics L.
Incze M.
Ujszaszy K.
J. Antibiot.
1984,
37:
836
6 Numbering of atoms throughout article
was attributed according to that of zincophorin 1 .
7a Labelle M.
Guindon Y.
J.
Am. Chem. Soc.
1989,
111:
2204
7b Guindon Y.
Yoakim C.
Gorys V.
Ogilvie WW.
Delorme D.
Renaud J.
Robinson G.
Lavallée JF.
Slassi A.
Jung G.
Rancourt J.
Durkin K.
Liotta D.
7c Guindon Y.
Slassi A.
Rancourt J.
Bantle G.
Bencheqroun M.
Murtagh L.
Ghiro E.
Jung G.
J. Org. Chem.
1995,
60:
288
8a Curran DP.
Shen W.
Zhang JC.
Heffner TA.
J.
Am. Chem. Soc.
1990,
112:
6738
8b Porter NA.
Rosenstein IJ.
Breyer RA.
Bruhnke JD.
Wu WX.
Mcphail AT.
8c Stack JG.
Curran DP.
Geib SV.
Rebek J.
Ballester P.
J. Am. Chem. Soc.
1992,
114:
7007
8d Sibi MP.
Ji JG.
Angew.
Chem., Int. Ed. Engl.
1996,
35:
190
8e Sibi MP.
Ji JG.
J.
Org. Chem.
1996,
61:
6090
9a Wu JH.
Radinov R.
Porter NA.
J.
Am. Chem. Soc.
1995,
117:
11029
9b Murakata M.
Jono T.
Mizuno Y.
Hoshino O.
J. Am. Chem. Soc.
1997,
119:
11713
9c Porter NA.
Wu JHL.
Zhang GR.
Reed AD.
J.
Org. Chem.
1997,
62:
6702
10a Hart DJ.
Huang HC.
Krishnamurthy R.
Schwartz T.
J.
Am. Chem. Soc.
1989,
111:
7507
10b Giese B.
Bulliard M.
Zeitz HG.
Synlett
1991,
425
10c Guindon Y.
Lavallée JF.
Boisvert L.
Chabot C.
Delorme D.
Yoakim C.
Hall D.
Lemieux R.
Simoneau B.
Tetrahedron
Lett.
1991,
32:
27
11a Guindon Y.
Faucher AM.
Bourque E.
Caron V.
Jung G.
Landry SR.
J.
Org. Chem.
1997,
62:
9276
11b Guindon Y.
Liu ZP.
Jung G.
J.
Am. Chem. Soc.
1997,
119 :
9289
11c Bouvier JP.
Jung G.
Liu ZP.
Guérin B.
Guindon Y.
Org. Lett.
2001,
3:
1391
12a Guindon Y.
Jung G.
Guérin B.
Ogilvie WW.
Synlett
1998,
213
12b Guindon Y.
Houde K.
Prévost M.
Cardinal-David B.
Landry SR.
Daoust B.
Bencheqroun M.
Guérin B.
J. Am. Chem. Soc.
2001,
123:
8496
12c Guindon Y.
Prévost M.
Mochirian P.
Guérin B.
Org. Lett.
2002,
4:
1019
12d Mochirian P.
Cardinal-David B.
Guérin B.
Prévost M.
Guindon Y.
Tetrahedron
Lett.
2002,
43:
7067
12e Brazeau JF.
Mochirian P.
Prévost M.
Guindon Y.
J. Org.
Chem.
2009,
74:
64
13a Guindon Y.
Lavallée JF.
Llinas-Brunet M.
Horner G.
Rancourt J.
J. Am.
Chem. Soc.
1991,
113:
9701
13b Guindon Y.
Guérin B.
Chabot C.
Ogilvie W.
J. Am. Chem. Soc.
1996,
118:
12528
13c Guindon Y.
Rancourt J.
J. Org. Chem.
1998,
63:
6554
14 Guérin B.
Chabot C.
Mackintosh N.
Ogilvie WW.
Guindon Y.
Can.
J. Chem.
2000,
78:
852
15 Corey EJ.
Helal CJ.
Angew. Chem. Int. Ed.
1998,
37:
1987
16 Bonadies F.
Cardilli A.
Lattanzi A.
Orelli LR.
Scettri A.
Tetrahedron
Lett.
1994,
35:
3383
17a Mulzer J.
Berger M.
Tetrahedron
Lett.
1998,
39:
803
17b Haustedt LO.
Panicker SB.
Kleinert M.
Hartung IV.
Eggert U.
Niess B.
Hoffmann HMR.
Tetrahedron
2003,
59:
6967
17c Kramp GJ.
Kim M.
Gais HJ.
Vermeeren C.
J. Am.
Chem. Soc.
2005,
127:
17910
17d Mulzer J.
Sieg A.
Brucher C.
Muller D.
Martin HJ.
Synlett
2005,
685
17e Gais HJ.
Kramp GJ.
Wolters D.
Reddy LR.
Chem.
Eur. J.
2006,
12:
5610
18 Sajiki H.
Tetrahedron
Lett.
1995,
36:
3465
19a Guindon Y.
Slassi A.
Ghiro E.
Bantle G.
Jung G.
Tetrahedron Lett.
1992,
33:
4257
19b Guindon Y.
Murtagh L.
Caron V.
Landry SR.
Jung G.
Bencheqroun M.
Faucher AM.
Guérin B.
J. Org. Chem.
2001,
66:
5427
20 Cardillo G.
Orena M.
Tetrahedron
1990,
46:
3321
21a Bartlett PA.
Meadows JD.
Brown EG.
Morimoto A.
Jernstedt KK.
J.
Org. Chem.
1982,
47:
4013
21b Duan JJW.
Smith AB.
J.
Org. Chem.
1993,
58:
3703
22 Laya MS.
Banerjee AK.
Cabrera EV.
Curr. Org. Chem.
2009,
13:
720
23 Tredwell M.
Luft JAR.
Schuler M.
Tenza K.
Houk KN.
Gouverneur V.
Angew.
Chem. Int. Ed.
2008,
47:
357
24a Inoue T.
Kitagawa O.
Oda Y.
Taguchi T.
J.
Org. Chem.
1996,
61:
8256
24b Guindon Y.
Soucy F.
Yoakim C.
Ogilvie WW.
Plamondon L.
J.
Org. Chem.
2001,
66:
8992
25 Broeker JL.
Hoffmann RW.
Houk KN.
J. Am. Chem. Soc.
1991,
113:
5006
26 Ligands on magnesium were not represented
for simplicity.
27 Ramachandran PV.
Prabhudas B.
Chandra JS.
Reddy MVR.
J. Org. Chem.
2004,
69:
6294
