Abstract
Methyl 5-azido-4-oxohexanoate was synthesized from 5-hexenoic acid in six steps and converted to the title compound by NaReO4 - and CF3 SO3 H-catalyzed reaction in Ac2 O/CCl4 followed by hydrolysis of the methyl ester moiety.
Key words
amides - antibiotics - azides - palladium - rhenium
References and Notes
1 Wachi M.
Iwai N.
Kunihisa A.
Nagai K.
Biochimie
1999,
81:
909
2 Awa A.
Iwai N.
Ueda T.
Suzuki K.
Asano S.
Yamagishi J.
Nagai K.
Wachi M.
Biosci. Biotechnol. Biochem.
2005,
69:
1721
3 Isono K.
Suzuki S.
J. Antibiot. Ser. A
1962,
15:
77
4a Onuki J.
Medeiros MH.
Bechara EJ.
Di Mascio P.
Biochim. Biophys. Acta
1994,
1225:
259
4b Neal R.
Yang P.
Fiechtl J.
Yildiz D.
Gurer H.
Ercal N.
Toxicol. Lett.
1997,
91:
169
4c Monteiro HP.
Abdalla DS.
Augusto O.
Bechara EJ.
Arch. Biochem. Biophys.
1989,
271:
206
5 Bowman RE.
Closier MD.
Islip PJ.
J. Chem. Soc.
1965,
470
6 Kobayashi Y.
Yoshida S.
Nakayama Y.
Eur. J. Org. Chem.
2001,
1873
7a Manis PA.
Rathke MW.
J. Org. Chem.
1980,
45:
4952
7b White JD.
Badger RA.
Kezar HS.
Pallenberg AJ.
Schiehser GA.
Tetrahedron
1989,
45:
6631
8 Effenberger F.
Beisswenger T.
Az R.
Chem. Ber.
1985,
118:
4869
9 Another sequence shown below produced (α-chloro)ethyl ketone i in low yield (Scheme
[2
10 Acid 6 is commercially available, but was conveniently prepared from cyclohexanone in 67% yield by oxidative ring cleavage with H2 O2 , FeSO4 , and CuSO4 .
[11
11 Ogibin YN.
Starostin EK.
Aleksandrov AV.
Pivnitsky KK.
Nikishin GI.
Synthesis
1994,
901
12 Starostin EK.
Ignotenko AV.
Lapitskaya MA.
Pivnitsky KK.
Nikishin GI.
Russ. Chem. Bull.
2001,
50:
833
13 Although the original procedure
[12 2 O was found to be quite successful.
14 Lambert C.
Utimoto K.
Nozaki H.
Tetrahedron Lett.
1984,
25:
5323
15 Chan DMT.
Marder TB.
Milstein D.
Taylor NJ.
J. Am. Chem. Soc.
1987,
109:
6385
