Abstract
In this paper we describe the synthesis of β,δ-diketoester substituted 1,7,9-undecatrienes and their intramolecular Diels-Alder (IMDA) cycloadditions under thermal and acid-catalysed conditions. Application of this chemistry in the synthesis of a solanapyrone D precursor is reported.
Key words
intramolecular Diels-Alder reaction - polyketide - solanapyrone D
References
1a
Jenkins KM.
Toske SG.
Jensen PR.
Fenical W.
Phytochemistry
1998,
49:
2299
1b
Oikawa H.
Yokota T.
Sakano C.
Suzuki Y.
Naya A.
Ichihara A.
Biosci. Biotechnol. Biochem.
1998,
62:
2016
1c
Ichihara A.
Tazaki H.
Sakamura S.
Tetrahedron Lett.
1983,
24:
5373
1d
Alam SS.
Bilton JN.
Slawin AMZ.
Williams DJ.
Sheppard RN.
Strange RN.
Phytochemistry
1989,
28:
2627
2 Two different structures have been assigned the name solanapyrone E,
[1]
here we use the notation E and E′ to distinguish them.
3a
Bahti P.
Strange RN.
Physiol. Mol. Plant Pathol.
2004,
64:
9
3b
Hamid K.
Strange RN.
Physiol. Mol. Plant Pathol.
2000,
56:
235
4a
Oikawa H.
Suzuki Y.
Katayama K.
Naya A.
Sakano C.
Ichihara A.
J. Chem. Soc., Perkin Trans. 1
1999,
1225
4b
Oikawa H.
Kobayashi T.
Katayama K.
Suzuki Y.
Ichihara A.
J. Org. Chem.
1998,
63:
8748
4c
Oikawa H.
Katayama K.
Suzuki Y.
Ichihara A.
J. Chem. Soc., Chem. Commun.
1995,
1321
4d
Oikawa H.
Suzuki Y.
Naya A.
Katayama K.
Ichihara A.
J. Am. Chem. Soc.
1994,
116:
3605
4e
Ichihara A.
Miki M.
Tazaki H.
Sakamura S.
Tetrahedron Lett.
1987,
28:
1175
5
Lygo B.
Bhatia M.
Cooke JWB.
Hirst DJ.
Tetrahedron Lett.
2003,
44:
2529
6 For an enantioselective amine-catalyzed Diels-Alder approach to solanapyrone D, see: Wilson RM.
Jen WS.
MacMillan DWC.
J. Am. Chem. Soc.
2005,
127:
11616
7
Hagiwara H.
Kobayashi K.
Miya S.
Hoshi T.
Suzuki T.
Ando M.
Okamoto T.
Kobayashi M.
Yamamoto I.
Ohtsubo S.
Kato M.
Uda H.
J. Org. Chem.
2002,
67:
5969
Lewis and Brønsted acid catalyzed Diels-Alder reactions involving 1-acyl-1,7,9-trienes generally give good levels of endo-selectivity, see for example:
8a
Morimoto Y.
Iwahashi M.
Kinoshita T.
Nishida K.
Chem. Eur. J.
2001,
7:
4107
8b
Evans DA.
Barnes DM.
Johnson JS.
Lectka T.
Matt P.
Miller SJ.
Murry JA.
Norcross RD.
Shaughnessy EA.
Campos KR.
J. Am. Chem. Soc.
1999,
121:
7582
8c
Iwasawa N.
Sugimori J.
Kawase Y.
Narasaka K.
Chem. Lett.
1989,
1947
8d
Evans DA.
Chapman KT.
Bisaha J.
J. Am. Chem. Soc.
1988,
110:
1238
8e
Roush WR.
Essenfeld AP.
Warmus JS.
Tetrahedron Lett.
1987,
28:
2447
8f
Roush WR.
Gillis HR.
Essenfeld AP.
J. Org. Chem.
1984,
49:
4674
8g
Roush WR.
Gillis HR.
J. Org. Chem.
1982,
47:
4825
9 For discussion of the thermal Diels-Alder chemistry of 1,7,9-trienes, see ref. 5 and references cited therein.
10 Compounds 3a-d were all prepared from (6E,8E)-deca-6,8-dienal.
[15]
See experimental section for further details.
11a
Yamaguchi M.
Shibato K.
Nakashima H.
Minami T.
Tetrahedron
1988,
44:
4767
11b
Harris TM.
Harris CM.
Tetrahedron
1977,
33:
2159
12
Hanamoto T.
Hiyama T.
Tetrahedron Lett.
1988,
29:
6467
13a
Lygo B.
Tetrahedron
1995,
51:
12859
13b
Lygo B.
Tetrahedron Lett.
1994,
35:
5073
14 For studies on the solid- and solution-phase structures of Al(acac)Cl2, see: Lewinski J.
Pasynkiewicz S.
Lipkowski J.
Inorg. Chim. Acta
1990,
178:
113
15a
Segi M.
Takahashi M.
Nakajima T.
Suga S.
Tetrahedron Lett.
1988,
29:
6965
15b
Ichihara A.
Miki M.
Tazaki H.
Sakamura S.
Tetrahedron Lett.
1987,
28:
1175
15c
Larsen SD.
Grieco PA.
J. Am. Chem. Soc.
1985,
107:
1768
