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For other significant efforts in this field that have not culminated in the synthesis of strychnine, see: a) S. F. Martin, C. W. Clark, M. Ito, M. Mortimore, J. Am. Chem. Soc. 1996, 118, 9804-9805;
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0001260770
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For a preliminary account of our synthesis of (-)-strychnine, see: D. Solé, J. Bonjoch, S. García-Rubio, E. Peidró, J. Bosch, Angew. Chem. 1999, 111, 408-410; Angew. Chem. Int. Ed. Engl. 1999, 38, 395-397.
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For a preliminary account of our synthesis of (-)-strychnine, see: D. Solé, J. Bonjoch, S. García-Rubio, E. Peidró, J. Bosch, Angew. Chem. 1999, 111, 408-410; Angew. Chem. Int. Ed. Engl. 1999, 38, 395-397.
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For reviews, see : a) J. Sapi, G. Massiot in Monoterpenoid Indole Alkaloids (Ed.: J.E. Saxton) in The Chemistry of Heterocyclic Compounds, Supplement to Vol. 25, Part 4 (Ed.: E. C. Taylor), Wiley, New York, 1994, pp. 279-355; b) J. Bosch, J. Bonjoch, M. Amat in The Alkaloids, Vol. 48 (Ed.: G. A. Cordell), Academic Press, New York, 1996, pp. 75-189.
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Sapi, J.1
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1542499040
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(Ed.: G. A. Cordell), Academic Press, New York
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For reviews, see : a) J. Sapi, G. Massiot in Monoterpenoid Indole Alkaloids (Ed.: J.E. Saxton) in The Chemistry of Heterocyclic Compounds, Supplement to Vol. 25, Part 4 (Ed.: E. C. Taylor), Wiley, New York, 1994, pp. 279-355; b) J. Bosch, J. Bonjoch, M. Amat in The Alkaloids, Vol. 48 (Ed.: G. A. Cordell), Academic Press, New York, 1996, pp. 75-189.
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Bosch, J.1
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22
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0013848559
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The numbering system and ring labeling based on the biogenetic interrelationship of indole alkaloids is used throughout this paper: J. Le Men, W. I. Taylor, Experientia 1965, 21, 508-510.
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Le Men, J.1
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a) J. Bonjoch, D. Solé, J. Bosch, J. Am. Chem. Soc. 1993, 115, 2064-2065;
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c) D. Solé, J. Bonjoch, J. Bosch, J. Org. Chem. 1996, 61, 4194-4195;
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d) D. Solé, J. Bonjoch, S. García-Rubio, R. Suriol, J. Bosch, Tetrahedron Lett. 1996, 37, 5213-5216;
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e) J. Bonjoch, D. Solé, S. García-Rubio, J. Bosch, J. Am. Chem. Soc. 1997, 119, 7230-7240.
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0343852937
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For other reports on the synthesis of Strychnos alkaloids in enantiopure form, see: a) M. Amat, M.-D. Coll, J. Bosch, E. Espinosa, E. Molins, Tetrahedron Asymmetry 1997, 8, 935-948; b) M. E. Kuehne, U. K. Bandarage, A. Hammach, Y.-L. Li, T. Wang, J. Org. Chem. 1998, 63, 2172-2183; c) S. Shimizu, K. Ohori, T. Arai, H. Sasai, M. Shibasaki, J. Org. Chem. 1998, 63, 7547-7551; d) M. E. Kuehne, F. Xu, J. Org. Chem. 1998, 63, 9434-9439. See also ref. [9a].
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Amat, M.1
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0001529989
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For other reports on the synthesis of Strychnos alkaloids in enantiopure form, see: a) M. Amat, M.-D. Coll, J. Bosch, E. Espinosa, E. Molins, Tetrahedron Asymmetry 1997, 8, 935-948; b) M. E. Kuehne, U. K. Bandarage, A. Hammach, Y.-L. Li, T. Wang, J. Org. Chem. 1998, 63, 2172-2183; c) S. Shimizu, K. Ohori, T. Arai, H. Sasai, M. Shibasaki, J. Org. Chem. 1998, 63, 7547-7551; d) M. E. Kuehne, F. Xu, J. Org. Chem. 1998, 63, 9434-9439. See also ref. [9a].
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Kuehne, M.E.1
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Li, Y.-L.4
Wang, T.5
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30
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0000221935
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For other reports on the synthesis of Strychnos alkaloids in enantiopure form, see: a) M. Amat, M.-D. Coll, J. Bosch, E. Espinosa, E. Molins, Tetrahedron Asymmetry 1997, 8, 935-948; b) M. E. Kuehne, U. K. Bandarage, A. Hammach, Y.-L. Li, T. Wang, J. Org. Chem. 1998, 63, 2172-2183; c) S. Shimizu, K. Ohori, T. Arai, H. Sasai, M. Shibasaki, J. Org. Chem. 1998, 63, 7547-7551; d) M. E. Kuehne, F. Xu, J. Org. Chem. 1998, 63, 9434-9439. See also ref. [9a].
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0032509232
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ref. [9a]
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For other reports on the synthesis of Strychnos alkaloids in enantiopure form, see: a) M. Amat, M.-D. Coll, J. Bosch, E. Espinosa, E. Molins, Tetrahedron Asymmetry 1997, 8, 935-948; b) M. E. Kuehne, U. K. Bandarage, A. Hammach, Y.-L. Li, T. Wang, J. Org. Chem. 1998, 63, 2172-2183; c) S. Shimizu, K. Ohori, T. Arai, H. Sasai, M. Shibasaki, J. Org. Chem. 1998, 63, 7547-7551; d) M. E. Kuehne, F. Xu, J. Org. Chem. 1998, 63, 9434-9439. See also ref. [9a].
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Kuehne, M.E.1
Xu, F.2
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33
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85037451166
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-
note
-
To our knowledge there are no precedents about the reactivity of α-alkoxypropargylic silanes with electrophiles.
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34
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0025111125
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H. Irie, K. Matsumoto, T. Kitagawa, Y. Zhang, Chem. Pharm. Bull. 1990, 38, 1451-1461.
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0346296856
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(Ed.: L. A. Paquette), Wiley, Chichester
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a) K. Suzuki, T. Nagasawa in Encyclopedia of Reagents for Organic Synthesis, Vol. 8 (Ed.: L. A. Paquette), Wiley, Chichester, 1995, pp. 5452-5453;
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Suzuki, K.1
Nagasawa, T.2
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0001528276
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For other procedures for the preparation of a-hydroxy silanes, see: R. L. Danheiser, D. M. Fink, K. Okano, Y.-M. Tsai, S. W. Szczepanski, J. Org. Chem, 1985, 50, 5393-5396; R. J. Linderman, Y. Suhr, J. Org. Chem. 1988, 53, 1569-1572.
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Danheiser, R.L.1
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Szczepanski, S.W.5
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38
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0000328254
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For other procedures for the preparation of a-hydroxy silanes, see: R. L. Danheiser, D. M. Fink, K. Okano, Y.-M. Tsai, S. W. Szczepanski, J. Org. Chem, 1985, 50, 5393-5396; R. J. Linderman, Y. Suhr, J. Org. Chem. 1988, 53, 1569-1572.
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Linderman, R.J.1
Suhr, Y.2
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40
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85037455816
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-
note
-
As racemic 2 was accessible in larger amounts than enantioenriched 2, these initial experiments were carried out with racemic material.
-
-
-
-
41
-
-
85037446348
-
-
note
-
13C NMR data with the aid of 2D-NMR (COSY, HMQC, HMBC, and NOESY) experiments.
-
-
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42
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0000558163
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[21c] a) H.-J. Knölker, N. Foitzik, H. Goesmann, R. Graf, Angew. Chem. 1993, 105, 1104-1106; Angew. Chem. Int. Ed. Engl. 1993, 32, 1081-1083; H.-J. Knölker, N. Foitzik, C. Gabler, R. Graf, Synthesis 1999, 145-151; J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345-2348;
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Knölker, H.-J.1
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33748819544
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[21c] a) H.-J. Knölker, N. Foitzik, H. Goesmann, R. Graf, Angew. Chem. 1993, 105, 1104- 1106; Angew. Chem. Int. Ed. Engl. 1993, 32, 1081-1083; H.-J. Knölker, N. Foitzik, C. Gabler, R. Graf, Synthesis 1999, 145-151; J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345-2348;
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44
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0344820772
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[21c] a) H.-J. Knölker, N. Foitzik, H. Goesmann, R. Graf, Angew. Chem. 1993, 105, 1104- 1106; Angew. Chem. Int. Ed. Engl. 1993, 32, 1081-1083; H.-J. Knölker, N. Foitzik, C. Gabler, R. Graf, Synthesis 1999, 145-151; J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345-2348;
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Knölker, H.-J.1
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0001159938
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[21c] a) H.-J. Knölker, N. Foitzik, H. Goesmann, R. Graf, Angew. Chem. 1993, 105, 1104- 1106; Angew. Chem. Int. Ed. Engl. 1993, 32, 1081-1083; H.-J. Knölker, N. Foitzik, C. Gabler, R. Graf, Synthesis 1999, 145-151; J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345-2348;
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b) R. L. Danheiser, B. R. Dixon, R. W. Gleason, J. Org. Chem. 1992, 57, 6094-6097;
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a) Radical cyclization : M. E. Kuehne, T. Wang, D. Seraphin, J. Org. Chem. 1996, 61, 7873-7881;
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0027231508
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b) Intramolecular Heck reaction: V. H. Rawal, C. Michoud, R. F. Monestel, J. Am. Chem. Soc. 1993, 115, 3030-3031;
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50
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85037477132
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2-promoted biscyclization: see ref. [11a,c,e]
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2-promoted biscyclization: see ref. [11a,c,e].
-
-
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51
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85037472360
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Intramolecular nucleophilic addition to an α,β-unsaturated ester: ref.[6b];
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a) Intramolecular nucleophilic addition to an α,β-unsaturated ester: see ref.[6b];
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52
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85037480997
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Intramolecular Heck reaction: see ref. [5b]
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b) Intramolecular Heck reaction: see ref. [5b].
-
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53
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0026620627
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For some examples of tandem cyclization-capture processes that involve the trapping of o-alkyl palladium species with different quenchers, see: a) CO as the quencher, R. Grigg, P. Kennewell, A. Teasdale, Tetrahedron Lett. 1992, 33, 7789-7792; E. Negishi, C. Coperet, S. Ma, T. Mita, T. Sugihara, J. M. Tour, J. Am. Chem. Soc. 1996, 118, 5904-5918; B. Crousse, L.-H. Xu, G. Bernardinelli, E. P. Kündig, Synlett 1998, 658-660;
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0030037592
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For some examples of tandem cyclization-capture processes that involve the trapping of o-alkyl palladium species with different quenchers, see: a) CO as the quencher, R. Grigg, P. Kennewell, A. Teasdale, Tetrahedron Lett. 1992, 33, 7789-7792; E. Negishi, C. Coperet, S. Ma, T. Mita, T. Sugihara, J. M. Tour, J. Am. Chem. Soc. 1996, 118, 5904-5918; B. Crousse, L.-H. Xu, G. Bernardinelli, E. P. Kündig, Synlett 1998, 658-660;
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For some examples of tandem cyclization-capture processes that involve the trapping of o-alkyl palladium species with different quenchers, see: a) CO as the quencher, R. Grigg, P. Kennewell, A. Teasdale, Tetrahedron Lett. 1992, 33, 7789-7792; E. Negishi, C. Coperet, S. Ma, T. Mita, T. Sugihara, J. M. Tour, J. Am. Chem. Soc. 1996, 118, 5904-5918; B. Crousse, L.-H. Xu, G. Bernardinelli, E. P. Kündig, Synlett 1998, 658-660;
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b) LiCN as the quencher, R. Grigg, V. Santhakumar, V. Sridharan, Tetrahedron Lett. 1993, 34, 3163-3164;
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d) vinylic stannanes as quenchers, B. Burns, R. Grigg, P. Ratananukul, V. Sridharan, P. Stevenson, S. Sukirthalingam, T. Worakun, Tetrahedron Lett. 1988, 29, 5565-5568; R. Larock, N. H. Lee, J. Org. Chem. 1991, 56, 6253-6254.
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d) vinylic stannanes as quenchers, B. Burns, R. Grigg, P. Ratananukul, V. Sridharan, P. Stevenson, S. Sukirthalingam, T. Worakun, Tetrahedron Lett. 1988, 29, 5565-5568; R. Larock, N. H. Lee, J. Org. Chem. 1991, 56, 6253-6254.
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Larock, R.1
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note
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[5b]
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62
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and references therein
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S. Bräse, A. de Meijere in Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 99- 166; J. T. Link, L. E. Overman in Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, 1998, pp. 231-269.
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Formation of 1,4-conjugate addition products in the Heck reaction with electron deficient olefins has also been explained by solvolysis of the palladium enolate. R. Benhaddou, S. Czernecki, G. Ville, J. Org. Chem. 1992, 57, 4612-4616; S.E. Denmark, M. E. Schnute, J. Org. Chem. 1995, 60, 1013-1019.
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66
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Formation of 1,4-conjugate addition products in the Heck reaction with electron deficient olefins has also been explained by solvolysis of the palladium enolate. R. Benhaddou, S. Czernecki, G. Ville, J. Org. Chem. 1992, 57, 4612-4616; S.E. Denmark, M. E. Schnute, J. Org. Chem. 1995, 60, 1013-1019.
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3SiH for the capture of alkylnickel intermediates in related processes, see : D. Solé, Y. Cancho, A. Llebaria, J. M. Moretó, A. Delgado, J. Org. Chem. 1996, 61, 5895-5904.
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[36b] of Strychnos alkaloids, a) M.-L. Bennasar, M. Alvarez, R. Lavilla, E. Zulaica, J. Bosch, J. Org. Chem. 1990, 55, 1156-1168;
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76
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see ref. [6a]
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b) see ref. [6a].
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The chemical shifts of our synthetic sample were coincident with those reported from a natural sample of the Wieland-Gumlich aldehyde: G. Massiot, B. Massoussa, M.-J. Jacquier, P. Thépénier, L. Le MenOlivier, C. Delaude, R. Verpoorte, Phytochemistry 1988, 27, 3293-3304.
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Massiot, G.1
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Verpoorte, R.7
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78
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note
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Starting from racemic 14 we also completed the synthesis of racemic Wieland-Gumlich aldehyde.
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79
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85037469895
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note
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[10] is used in the NMR assignments.
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