Abstract
A synthesis of the C14-C28 fragment of Tetronasin features an SE 2 reaction between a cationic η3 -allylmolybdenum complex and and an α-metallated tetrahydrofuran.
Keywords
π-allyl complex - molybdenum - copper - substitution
References
1
Davies DH.
Snape EW.
Suter PJ.
King TJ.
Falshaw CP.
J. Chem. Soc., Chem. Commun.
1981,
1073
2
Keller-Julsen C.
King HD.
Kuhn M.
Loosli HR.
Pache W.
Petcher TJ.
Weber HP.
von Wartburg A.
J. Antibiot.
1982,
35:
142
3
Newbold CJ.
Wallace RJ.
Watt ND.
Richardson AJ.
Appl. Environ. Microbiol.
1988,
54:
544
4
Gates RN.
Roland LT.
Wyatt WE.
Hembry FG.
Bailie JH.
J. Anim. Sci.
1989,
67:
3419
5
Hori K.
Hikage N.
Inagaki A.
Mori S.
Nomura K.
Yoshii E.
J. Org. Chem.
1992,
57:
2888
6
Hori K.
Kazuno H.
Nomura K.
Yoshii E.
Tetrahedron Lett.
1993,
34:
2183
7
Hori K.
Mori S.
Nomura K.
Inagaki A.
Yoshii E.
Chem. Pharm. Bull.
1990,
38:
1784
8
Hori K.
Nomura K.
Kazuno H.
Yoshii E.
Chem. Pharm. Bull.
1990,
38:
1778
9
Ley SV.
Clase JA.
Mansfield DJ.
Osborn HMI.
J. Heterocycl. Chem.
1996,
33:
1533
10
De Laszlo SE.
Ford MJ.
Ley SV.
Maw GN.
Tetrahedron Lett.
1990,
31:
5525
11
Ley SV.
Brown DS.
Clase JA.
Fairbanks AJ.
Lennon IC.
Osborn HMI.
Stokes ESE.
Wadsworth DJ.
J. Chem. Soc., Perkin Trans. 1
1998,
2259
12
Ley SV.
Wadsworth DJ.
Tetrahedron Lett.
1989,
30:
1001
13
Ley SV.
Trudell ML.
Wadsworth DJ.
Tetrahedron
1991,
47:
8285
14
Semmelhack MF.
Kim CR.
Dobler W.
Meier M.
Tetrahedron Lett.
1989,
30:
4925
15
Semmelhack MF.
Epa WR.
Cheung AW.-H.
Gu Y.
Kim C.
Zhang N.
Lew W.
J. Am. Chem. Soc.
1994,
116:
7455
16
Lee HW.
Lee IYC.
Kim SK.
Tetrahedron Lett.
1990,
31:
7637
17
Lee HW.
Lee IYC.
Synlett
1991,
871
18
Hill RK.
Foley PJ.
Gardella LA.
J. Org. Chem.
1967,
32:
2330
19
Wolinsky J.
Chan D.
J. Org. Chem.
1965,
30:
41
20
Kraus GA.
Molina MT.
J. Org. Chem.
1988,
53:
752
21
Kraus GA.
Frazier KA.
Roth BD.
Taschner MJ.
Neuenschwander K.
J. Org. Chem.
1981,
46:
2417
22
Cooksey J.
Gunn A.
Kocienski PJ.
Kuhl A.
Uppal S.
Christopher JA.
Bell R.
Org. Biomol. Chem.
2004,
2:
1719
23
Kolb HC.
Van Nieuwenhze MS.
Sharpless KB.
Chem. Rev.
1994,
94:
2483
24
Mitsunobu O.
Synthesis
1981,
1
25
Hughes DL.
Org. React. (N.Y.)
1992,
42:
335
26 The five- and six-membered lactones were easily distinguished by their characteristic 13 C NMR signals for the C=O groups at δ = 178.1 and 171.2, respectively.
27
Cohen T.
Lin M.-T.
J. Am. Chem. Soc.
1984,
106:
1130
28
Cohen T.
Bhupathy M.
Acc. Chem. Res.
1989,
22:
152
29
Rychnovsky SD.
Plzak K.
Pickering D.
Tetrahedron Lett.
1994,
35:
6799
30
Christopher JA.
Kocienski P.
Procter M.
Synlett
1998,
425
31
Freeman PK.
Hutchinson LL.
J. Org. Chem.
1980,
45:
1924
32 A pure sample of (23R )-21 could not be obtained; therefore the NOE data was recorded on a mixture enriched in (23R )-21 .
33
Sawyer JS.
Kucerovy A.
Macdonald TL.
McGarvey GJ.
J. Am. Chem. Soc.
1988,
110:
842
34 Compound (23R )-27 is an intermediate in the Yoshii synthesis of Tetronomycin (see ref. 5).
35
Zhao Y.
Beddoes RL.
Quayle P.
Tetrahedron Lett.
1994,
35:
4183
36
Amano S.
Fujiwara K.
Murai A.
Chem. Lett.
1998,
409
37
Kocienski PJ.
Bell R.
Bourque E.
Christopher JA.
Cooksey J.
Gunn A.
Kuhl A.
Li Y.
Uppal S.
Yuen J.
Pure Appl. Chem.
2004,
76:
477
38
Faller JW.
Linebarrier D.
Organometallics
1988,
7:
1670
39
Faller JW.
Lambert C.
Mazzieri MR.
J. Organomet. Chem.
1990,
383:
161
40 Loss of stereochemical integrity has been observed in the conjugate addition of chiral α-alkoxyalkylcuprates to enones and propiolate esters: Linderman RJ.
Griedel BD.
J. Org. Chem.
1990,
55:
5428