Abstract
Domino oxidation of primary alcohols to α,β-unsaturated compounds using the combination
of PCC-NaOAc and stabilized Wittig reagent and its application towards total synthesis
of ABT-418 and 4-oxonon-2-enoic acid is described.
Keywords
primary alcohols - oxidation - PCC - olefination - domino reaction
References
<A NAME="RZ03404SS-1">1</A>
Tietze LF.
Chem. Rev.
1996,
96:
195
<A NAME="RZ03404SS-2">2</A>
Ireland RE.
Norbeck DW.
J. Org. Chem.
1985,
50:
2198
<A NAME="RZ03404SS-3A">3a</A>
Wei X.
Taylor RJK.
Tetrahedron Lett.
1998,
3815
<A NAME="RZ03404SS-3B">3b</A>
Blackburn L.
Wei X.
Taylor RJK.
Chem. Commun.
1999,
1337
<A NAME="RZ03404SS-3C">3c</A>
Wei X.
Taylor RJK.
J. Org. Chem.
2000,
65:
616
<A NAME="RZ03404SS-3D">3d</A>
Davies SB.
McKervey MA.
Tetrahedron Lett.
1999,
40:
1229
<A NAME="RZ03404SS-3E">3e</A>
Shuto S.
Niizuma S.
Matsuda A.
J. Org. Chem.
1998,
63:
4489
<A NAME="RZ03404SS-3F">3f</A>
Crich D.
Mo X.-S.
Synlett
1999,
67
<A NAME="RZ03404SS-3G">3g</A>
Huang CC.
J. Labeled Compd. Radiopharm.
1987,
24:
675
<A NAME="RZ03404SS-3H">3h</A>
Barrett AGM.
Humprecht D.
Ohkubo M.
J.Org. Chem.
1997,
62:
9376
<A NAME="RZ03404SS-4">4</A>
Tilve SG.
Desai VG.
Synth. Commun.
1999,
29:
3017
<A NAME="RZ03404SS-5A">5a</A>
Garvey DS.
Wasicak JT.
Deckar MW.
Brioni JD.
Buckely MJ.
Sullivan JP.
Carrera GM.
Holladay MW.
Arneric SP.
Williams M.
J. Med. Chem.
1994,
37:
1055
<A NAME="RZ03404SS-5B">5b</A>
Elliott RL.
Kopecka H.
Lin N.-H.
He Y.
Gravey DS.
Synthesis
1995,
772
<A NAME="RZ03404SS-5C">5c</A>
Wittenberger SJ.
J. Org. Chem.
1996,
61:
356
<A NAME="RZ03404SS-5D">5d</A>
Lin N.-H.
He Y.
Kopecka H.
Tetrahedron Lett.
1995,
2563
<A NAME="RZ03404SS-5E">5e</A>
Bunnelle WH.
Singam PR.
Narayan BA.
Bradshaw CW.
Liou JS.
Synthesis
1997,
439
<A NAME="RZ03404SS-6">6</A>
Corey EJ.
Suggs JJW.
Tetrahedron Lett.
1975,
2647
<A NAME="RZ03404SS-7A">7a</A>
Ando K.
J. Org. Chem.
1997,
62:
1934
<A NAME="RZ03404SS-7B">7b</A>
Brown HC.
Bhat NG.
Campbell B.
J. Org. Chem.
1986,
51:
3398
<A NAME="RZ03404SS-7C">7c</A>
Gibson TW.
Erman WF.
J. Org. Chem.
1972,
37:
1148
<A NAME="RZ03404SS-7D">7d</A>
Registry No. 54340-72-6.
<A NAME="RZ03404SS-7E">7e</A>
Katzenellenbrogen JA.
Utawanit T.
J. Am. Chem. Soc.
1974,
96:
6153
<A NAME="RZ03404SS-7F">7f</A>
Cavallo AS.
Koessler JL.
J. Org. Chem.
1994,
59:
3240
<A NAME="RZ03404SS-7G">7g</A>
Tomizawa K.
Watt DS.
Synthesis
1985,
887
<A NAME="RZ03404SS-7H">7h</A>
Vogel’s Textbook of Practical Organic Chemistry; Longman, 5th ed., 1989, 1033.
<A NAME="RZ03404SS-7I">7i</A>
Pietrusiewiez KM.
Monkiewiez J.
Tetrahedron Lett.
1986,
739
<A NAME="RZ03404SS-8">8</A>
Arneric SP.
Anderson DJ.
Bannon AW.
Briggs CA.
Buccafusco JJ.
Brioni J.
Cannon JB.
Decker MW.
Donnelly-Roberts D.
Gopalakrishnan M.
Holladay MW.
Kyncl J.
Marsh KC.
Pauly J.
Radek RJ.
Rodrigues AD.
Sullivan JP.
Cent. Nerv. Syst. Drug Rev.
1995,
1:
1
<A NAME="RZ03404SS-9">9</A>
Buchi G.
Vederas JC.
J. Am. Chem. Soc.
1972,
94:
9128
<A NAME="RZ03404SS-10">10</A>
Ballini R.
Bosica G.
J. Nat. Prod.
1998,
61:
673
<A NAME="RZ03404SS-11">11</A>
Obrect D.
Weiss B.
Helv. Chim. Acta
1989,
72:
117
<A NAME="RZ03404SS-12">12</A>
Enantiomeric purity of the products ethyl (2S)-2-[(1E)-3-oxobut-1-enyl]pyrrolidine-1-carboxylate, 3-methyl-5-(carboethoxy)pyrrolidinyl
isoxazole, 3-methyl-5-[1-methyl-2-(S)-pyrrolidinyl] isoxazole (ABT-418) were determined on chiral AD-column as reported
in an earlier synthesis (see reference 5b).
