Organic Letters
Letter
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9) For previous syntheses of lepadiformine A, see: (a) Abe, H.;
Aoyagi, S.; Kibayashi, C. Angew. Chem., Int. Ed. 2002, 41, 3017.
b) Abe, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2005, 127,
suspect the efficiency may be among the highest of prior approaches,
but cannot be certain.
(
1
1
473. (c) Bagley, M. C.; Oppolzer, W. Tetrahedron: Asymmetry 2000,
1, 2625. (d) Greshock, T. J.; Funk, R. L. Org. Lett. 2001, 3, 3511.
(
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e) Kibayashi, C.; Aoyagi, S.; Abe, H. Bull. Chem. Soc. Jpn. 2003, 76,
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10) For total syntheses of fasicularin, see: (a) Abe, H.; Aoyagi, S.;
Kibayashi, C. J. Am. Chem. Soc. 2000, 122, 4583. (b) Greshock, T. J.;
Funk, R. L. Org. Lett. 2001, 3, 3511. For syntheses of the cylindricines,
see: (c) Snider, B. B.; Liu, T. J. Org. Chem. 1997, 62, 5630.
(
(
d) Molander, G. A.; Ro
e) Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 4599. (f) Arai, T.;
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Org. Chem. 2005, 70, 3898. (k) Shibuguchi, T.; Mihara, H.;
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1
997, 62, 5630. (m) See ref 9n. (n) Wang, J.; Swidorski, J. J.;
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14) Abe, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2005, 127,
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(
(
1
(
(
(
c) Kessar, S. V.; Singh, P.; Kaur, A.; Singh, S. ARKIVOC 2003, 3, 120.
d) Kessar, S. V.; Singh, P.; Singh, K. N.; Dutt, M. J. Am. Chem. Soc.
2
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007, 129, 4506.
16) Perry, M. A.; Morin, M. D.; Slafer, B. W.; Rychnovsky, S. D. J.
Org. Chem. 2012, 77, 3390.
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18) This side chain can effectively control stereochemistry in a
(
4
(
conceptually related double aza-Michael addition, albeit with a
different relative stereochemical outcome. See ref 10d.
(
19) Jackson, R. F. W.; Moore, R. J.; Dexter, C. S.; Elliott, J. S.;
Mowbray, C. E. J. Org. Chem. 1998, 63, 7875.
20) The efficiency of ref 14 cannot be evaluated because the
(
synthesis of its noncommercial, nontrivial starting material, (5E,7E)-
tetradeca-5,7-dien-1-ylmagnesium bromide, is not reported. Based on
the 31% overall yield to (−)-1 starting from this Grignard reagent, we
D
Org. Lett. XXXX, XXX, XXX−XXX