J. Barbion et al. / Tetrahedron 68 (2012) 6504e6512
6511
€
Int. Ed. Engl. 1986, 25, 160e162; (d) Kramer, T.; Hoppe, D. Tetrahedron Lett. 1987,
This work was partly supported by grants from the Swedish
Research Council (Grants 621-2009-4736 and 622-2009-371). S.S.
thanks the Wenner-Gren Foundations for a postdoctoral fellowship.
Computer time was generously provided by the PDC Center for
High Performance Computing.
€
28, 5149e5152; (e) Kramer, T.; Scharwark, J.-R.; Hoppe, D. Tetrahedron Lett.
1989, 30, 7037e7040; (f) Schwark, J. R.; Hoppe, D. Synthesis 1990, 291e294; (g)
See Ref. 6d. For allyltitanation of aldehydes from optically active aliphatic
secondary allylcarbamates see: (h) Razon, P.; Dhulut, S.; Bezzenine-Lafollee, S.;
Courtieu, J.; Pancrazi, A.; Ardisson, J. Synthesis 2005, 102e108; (i) Razon, P.;
N’Zoutani, M.-A.; Dhulut, S.; Bezzenine-Lafollee, S.; Courtieu, J.; Pancrazi, A.;
ꢀ
ꢀ
Ardisson, J. Synthesis 2005, 109e121 For allyltitanation of aldehydes from op-
tically active cyclic secondary allylcarbamates see: (j) Becker, J.; Grimme, S.;
Supplementary data
€
Frolich, R.; Hoppe, D. Angew. Chem. 2007, 119, 1672e1676; Angew. Chem., Int. Ed.
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2007, 46, 1645e1649; (k) Becker, J.; Frolich, R.; Kataeva, O.; Hoppe, D. Eur. J. Org.
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Supplementary data associated with this article can be found, in
Chem. 2007, 3349e3364; (l) Becker, J.; Bergander, K.; Frolich, R.; Hoppe, D.
Angew. Chem. 2008, 120, 1678e1681; Angew. Chem., Int. Ed. 2008, 47,
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1654e1657; (m) Hemery, T.; Becker, J.; Frolich, R.; Hoppe, D. Eur. J. Org. Chem.
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2010, 3711e3720; (n) Hemery, T.; Wibbeling, B.; Frolich, R.; Hoppe, D. Synthesis
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Chelain, E.; Pancrazi, A.; Ardisson, J.; Fahy, J. Eur. J. Org. Chem. 2007, 5235e5243.
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References and notes
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9. Earlier investigations relied on the simultaneous control of C2 and C3 cen-
tres through allylation reaction of the corresponding bulky methylketone
with allylcarbamate (ꢀ)-11, under Hoppe conditions, have been conducted to
provide directly the desired racemic homoallylic alcohol. Unfortunately, de-
spite several attempts, no reaction occurred; the starting material was re-
covered along with degradation products. The methylketone was smoothly
obtained from aldehyde 13 by methylation and subsequent Swern oxidation.
2. Salinosporamide syntheses: for reviews see: (a) Gulder, T. A.; Moore, B. S. An-
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10.
Methylation of pyrrolidin-3-ones (salinosporamide numbering): Mono-
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D-arabinose de-
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conformers.
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1990, 29, 336e337; Angew. Chem., Int. Ed. Engl. 1990, 29, 296e298; (b) Zschage,
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14. To overcome this unfavourable diastereoselectivity, different methylation
conditions of ketones without spiroketal moiety were screened without any
satisfactory result.
€
O.; Schwark, J. R.; Kramer, T.; Hoppe, D. Tetrahedron 1992, 48, 8377e8388 For
crotyltitanation of aldehydes from optically active secondary crotylcarbamates
€
see: (c) Hoppe, D.; Kramer, T. Angew. Chem. 1986, 29, 171e173; Angew. Chem.,