Tremorgenic indole alkaloids. 10. An improved asymmetric synthesis of a tricyclic common intermediate

Israel Journal of Chemistry

Volumn 37, Issue 1, 1997, Pages 69-80

  Smith III, Amos B ^a   Hartz, Richard A ^a   Spoors, P Grant ^a   Rainier, Jon D ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031527409     PISSN: 00212148     EISSN: None     Source Type: Journal    
DOI: 10.1002/ijch.199700009     Document Type: Article

References (80)

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51. σ-Bond construction of trisubstituted olefins is a unifying theme in our recent syntheses of FK506, rapamycin, and discodermolide; for leading references see: Smith, A.B., III; Chen, K; Robinson, D.J.; Laasko, L.M.; Hale, K.L. Tetrahedron Lett. 1994, 35, 4271; Smith, A.B., III; Condon, S.M.; McCauley, J.A.; Leazer, J.L., Jr.; Leahy J.W.; Maleczka, R.E. J. Am. Chem. Soc. 1997, 119, 947; Smith, A.B., III; Condon, S.M.; McCauley, J.A.; Leazer, J.L., Jr.; Leahy, J.W.; Maleczka, R.E. J. Am. Chem. Soc. 1997, 119, 962-973. Smith, A.B., III; Qiu, Y.; Jones, D.R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011.
52. σ-Bond construction of trisubstituted olefins is a unifying theme in our recent syntheses of FK506, rapamycin, and discodermolide; for leading references see: Smith, A.B., III; Chen, K; Robinson, D.J.; Laasko, L.M.; Hale, K.L. Tetrahedron Lett. 1994, 35, 4271; Smith, A.B., III; Condon, S.M.; McCauley, J.A.; Leazer, J.L., Jr.; Leahy J.W.; Maleczka, R.E. J. Am. Chem. Soc. 1997, 119, 947; Smith, A.B., III; Condon, S.M.; McCauley, J.A.; Leazer, J.L., Jr.; Leahy, J.W.; Maleczka, R.E. J. Am. Chem. Soc. 1997, 119, 962-973. Smith, A.B., III; Qiu, Y.; Jones, D.R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011.
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76. 4.
77. 1H NMR (500 MHz).
78. Materials and Methods. All reactions were carried out in flame-or oven-dried glassware under an argon atmosphere with dry, freshly distilled solvents, unless otherwise indicated. Tetrahydrofuran and diethyl ether were distilled under argon from sodium/benzophenone. Dichloromethane was distilled from calcium hydride. Triethylamine, diisopropylamine, N,N-diisopropylethylamine, DBU, and DMPU were dried and distilled from calcium hydride and stored over KOH. Anhydrous t-butanol and nitromethane were dried and distilled from calcium hydride and stored over 4-Å molecular sieves. Methyllithium was purchased from Aldrich and standardized by titration with diphenylacetic acid. All reactions were monitored by TLC using E. Merck 0.25-mm precoated silica gel plates. Flash chromatography was performed with the indicated solvents and silica gel-60 (particle size 0.040-0.062 mm) supplied by E. Merck. Yields refer to chromatographically and spectroscopically pure compounds unless otherwise stated. The instrumentation described in ref 1 was again em3 ployed in this work.
79. Preparation of zinc-copper couple: LeGoff, E. J. Org. Chem. 1964, 29, 2048. Following the acetic acid wash described by LeGoff, the zinc-copper couple was washed with water (5×), ethanol (4×), and then ether (5×).
80. The buffer solution was prepared by addition of 3 M aqueous formic acid (25.8 mL) to 3 M KOH (9.6 mL) and dilution to 100 mL.