Total synthesis of (+)-cocaine via desymmetrization of a meso-dialdehyde

Organic Letters

Volumn 6, Issue 19, 2004, Pages 3305-3308

  Mans, Douglas M ^a   Pearson, William H ^a,b  

^a UNIVERSITY OF MICHIGAN   (United States)

^b Berry and Associates Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; COCAINE; LITHIUM DERIVATIVE; PROLINE; PYRROLIDINE DERIVATIVE; TROPANE DERIVATIVE;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLOADDITION; REACTION ANALYSIS; SYNTHESIS;

ALDEHYDES; CATALYSIS; COCAINE; CYCLIZATION; MOLECULAR STRUCTURE; PROLINE; PYRROLIDINES; STEREOISOMERISM;

EID: 4644291195     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048777a     Document Type: Article

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72. A similar sequence with 15eq would lead to the synthesis of pseudococaine.
73. 3)].
74. 3). Although by no means definitive, these results seem to indicate that 15eq (arising from aldol 13eq) would lead to the (+)-isomer of pseudococaine with an ee similar to that obtained for (+)-cocaine.
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77. For experimental and theoretical work on the proline-catalyzed aldol transition states, see: (a) Bahmanyar, S.; Houk. K. N. J. Am. Chem. Soc. 2001, 123, 9922. (b) Bahmanyar, S.; Houk, K. N. J. Am. Chem. Soc. 2001, 123, 11273. (c) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475. (d) Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16.
78. For experimental and theoretical work on the proline-catalyzed aldol transition states, see: (a) Bahmanyar, S.; Houk. K. N. J. Am. Chem. Soc. 2001, 123, 9922. (b) Bahmanyar, S.; Houk, K. N. J. Am. Chem. Soc. 2001, 123, 11273. (c) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475. (d) Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16.
79. For experimental and theoretical work on the proline-catalyzed aldol transition states, see: (a) Bahmanyar, S.; Houk. K. N. J. Am. Chem. Soc. 2001, 123, 9922. (b) Bahmanyar, S.; Houk, K. N. J. Am. Chem. Soc. 2001, 123, 11273. (c) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475. (d) Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16.
80. A dihedral angle of 180° is termed and, while an angle of 0° refers to the syn arrangement.
81. Preliminary investigations to test the rationale with other N-protecting groups (i.e. N-H, N-Me, and N-CHO) were thwarted as attempted oxidation to the meso-dialdehyde led only to the recovery of starting material or decomposition products. Another possibility not investigated by us would be to use a proline derivative incapable of forming such H-bonds such as the methyl ester of L-proline to see if any asymmetric induction occurs at all.
82. One must consider the issues of the E/Z enamine geometry, boat/ chair conformations, synlanti relationship of the carboxylic acid to the olefin, equatorial versus axial placement of substituents, and the issue of H-bond acceptor (Boc carbonyl versus aldehyde) quickly causes the number of reasonable transition states possible to become extremely large. See ref 31 for more detailed discussions.
83. Based on these rationale, one would expect to obtain (-)-cocaine if D-proline was used instead.