Abstract
Spiroepoxy lactones 2 and 3 were obtained by epoxidation of α-alkylidenelactones 1 with dimethyldioxirane. Reaction of spiroepoxy
lactones 2 with binucleophiles gave access
to a number of hydroxyalkyl heterocycles with interesting substituent
patterns. Depending on both the kind of substituent at the oxirane
ring as well as the type of the binucleophile, the spiroepoxy lactones
react either as C3 or as C2 bielectrophilic
building blocks giving 4-, 6- and 7-membered partially saturated
N-and S-heterocycles 5, 6, 8, 9, 11 and 13.
Key words
epoxidations - ring transformation - thiazepinones - diazepinones - 1,4-thiazinones
- benzothiopyranones - β-lactams
References
<A NAME="RT01103SS-1">1</A>
Otto A.
Ziemer B.
Liebscher J.
Eur. J.
Org. Chem.
1998,
2667
<A NAME="RT01103SS-2">2</A>
Otto A.
Ziemer B.
Liebscher J.
Synthesis
1999,
965
<A NAME="RT01103SS-3">3</A>
Otto A.
Abegaz B.
Ziemer B.
Liebscher J.
Tetrahedron: Asymmetry
1999,
10:
3381
<A NAME="RT01103SS-4">4</A>
Otto A.
Liebscher J.
J. Heterocycl. Chem.
2000,
37:
891
<A NAME="RT01103SS-5">5</A>
Woydowski K.
Ziemer B.
Liebscher J.
J.
Org. Chem.
1999,
64:
3489
<A NAME="RT01103SS-6">6</A>
Woydowski K.
Liebscher J.
Tetrahedron
1999,
55:
9205
<A NAME="RT01103SS-7">7</A>
Woydowski K.
Liebscher J.
Synthesis
1998,
1110
<A NAME="RT01103SS-8">8</A>
Woydowski K.
Ziemer B.
Liebscher J.
Tetrahedron: Asymmetry
1998,
9:
1231
<A NAME="RT01103SS-9">9</A>
Woydowski K.
Liebscher J.
J. Prakt. Chem.
1998,
340:
567
<A NAME="RT01103SS-10">10</A>
Woydowski K.
Fleischhauer J.
Schiffer J.
Liebscher J.
J. Chem. Soc., Perkin Trans.
1
1999,
149
<A NAME="RT01103SS-11">11</A>
Bohlmann F.
Fritz U.
King RM.
Robinson H.
Phytochemistry
1981,
20:
743
<A NAME="RT01103SS-12">12</A>
Fischer NH.
Lee IY.
Fronczek FR.
Chiari G.
Urbatsch LE.
J. Nat. Prod.
1984,
47:
419
<A NAME="RT01103SS-13">13</A>
Sohoni JS.
Rojatkar SR.
Kulkarni MM.
Dhaneshwar NN.
Tavale SS.
Gururow TN.
Nagasampagi BA.
J. Chem. Soc.,
Perkin Trans. 1
1988,
157
<A NAME="RT01103SS-14">14</A>
Borges del Castillo J.
Manresa Ferrero MT.
Rodriguez Luis F.
Rodriguez Ubis JC.
Vazquez Bueno P.
Rev. Latinoam. Quim.
1984,
15:
96 ; Chem. Abstr. 1985, 102, 182384
<A NAME="RT01103SS-15">15</A>
Trost BM.
Arndt HC.
J. Org. Chem.
1973,
38:
3140
<A NAME="RT01103SS-16">16</A>
White JD.
Bremner JB.
Dimsdale MJ.
Garcea RL.
J.
Am. Chem. Soc.
1971,
93:
281
<A NAME="RT01103SS-17">17</A>
Shibata I.
Yamasaki H.
Baba A.
Matsuda H.
J. Org. Chem.
1992,
57:
6909
<A NAME="RT01103SS-18">18</A>
Guseinov FI.
Tagiev SSh.
Moskva VV.
Zh. Org. Khim.
1995,
31:
96
<A NAME="RT01103SS-19">19</A>
Murray AW.
Reid RG.
Synthesis
1985,
35
<A NAME="RT01103SS-20">20</A>
Strobach DR.
Carbohydr.
Res.
1971,
17:
457
<A NAME="RT01103SS-21">21</A>
Yamauchi S.
Kinoshita Y.
Biosci., Biotech. Biochem.
1998,
62:
1726
<A NAME="RT01103SS-22">22</A>
Bertounesque E.
Millal F.
Meresse Ph.
Monneret C.
Tetrahedron: Asymmetry
1998,
9:
2999
<A NAME="RT01103SS-23">23</A>
Akbutina FA.
Sadretdinov IF.
Vasile’va EV.
Miftakhov MS.
Russ.
J. Org. Chem.
2000,
36:
1823
<A NAME="RT01103SS-24">24</A>
Stachel HD.
Poschenrieder H.
Burghard H.
Z. Naturforsch.
1980,
35B:
724
<A NAME="RT01103SS-25">25</A>
Peng H.
Kim D.-I.
Sarkaria JN.
Cho Y.-S.
Abraham RT.
Zalkow LH.
Bioorg. Med. Chem.
2002,
10:
167
<A NAME="RT01103SS-26">26</A>
Bartels A.
Jones PG.
Liebscher J.
Tetrahedron: Asymmetry
1995,
6:
1539
<A NAME="RT01103SS-27">27</A>
Panfiel J.
Chmielewski M.
Belzencki C.
Heterocycles
1986,
6:
1609
<A NAME="RT01103SS-28">28</A>
Pätzel M.
Ushmajev A.
Liebscher J.
Synthesis
1993,
525 ; and references cited therein
<A NAME="RT01103SS-29">29</A>
Adam W.
Bialas J.
Hadjiarapoglou L.
Chem.
Ber.
1991,
124:
2377
<A NAME="RT01103SS-30">30</A>
Full details have been deposited with
the Cambridge Crystallographic Data Centre as supplementary publication no.
CCDC-205880. Copies of the data can be obtained free of charge on
apllication to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK.
