Synthetic studies on actinobolin and bactobolin: Synthesis of N-desalanyl-N-[2-(trimethylsilyl)ethanesulfonyl] derivatives from a common intermediate and attempted removal of the SES protecting group

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5498-5505

  Ward, Dale E ^a   Gai, Yuanzhu ^a   Kaller, Brian F ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACTINOBOLIN; BACTOBOLIN;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029741481     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960579c     Document Type: Article

References (66)

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24. For other synthetic studies on actinobolins see: (a) Rao, M. V.; Nagarajan, M. Indian J. Chem. 1988, 27B, 718. (b) Kates, S. A. Ph.D. Thesis, Brandeis University, Waltham, MA, 1988; Diss. Abstr. Int. B 1989, 49, 2651.
25. For other synthetic studies on actinobolins see: (a) Rao, M. V.; Nagarajan, M. Indian J. Chem. 1988, 27B, 718. (b) Kates, S. A. Ph.D. Thesis, Brandeis University, Waltham, MA, 1988; Diss. Abstr. Int. B 1989, 49, 2651.
26. For other synthetic studies on actinobolins see: (a) Rao, M. V.; Nagarajan, M. Indian J. Chem. 1988, 27B, 718. (b) Kates, S. A. Ph.D. Thesis, Brandeis University, Waltham, MA, 1988; Diss. Abstr. Int. B 1989, 49, 2651.
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31. (b) Also see ref 5d.
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34. A preliminary account has been reported: Ward, D. E.; Gai, Y.; Kaller, B. F. Tetrahedron Lett. 1994, 35, 3485.
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39. Stereoisomers of 20 were not detected in the reaction mixture.
40. Increasing the reaction time to 1 h did not improve the yield of 20; however, diol (∼10%) was detected in the reaction mixture. A larger scale reaction run at higher concentration on material derived from degradation of actinobolin gave 19 in 87% yield (see Experimental Section).
41. We use this term to describe a diastereoselective synthesis of a specific enantiomer as opposed to a diastereoselective synthesis of a racemate or an atiantioselective synthesis. For example, see: Ward, R. S. Chem. Br. 1991, 27, 803.
42. We thank the Parke-Davis Pharmaceutical Research Divison of Warner-Lambert Co. for a generous gift of actinobolin sulfate.
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45. 3N; thus a 1.3:1 mixture of EtOH and EtOAc was used as the medium for acylation with BnOCOCl.
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47. Molecular mechanics using the MM2 forcefield included in the CAChe Worksystem (version 3.7 from CAChe Scientific Inc.). Structures were minimized with the Newton-Raphson block diagonal method to 0.001 kcal/mol convergence. Relevant minima were located by minimizing at least 10 initial conformations generated from driving the dihedral angles for each rotatable bond.
48. E = 104°, distance 3-4 = 2.35 Å.
49. E = 128°.
50. E = 112° (this conformation was 10.1 kcal/mol above the global minimum).
51. 3 in a 1.05:1 molar ratio with respect to MeLi (as opposed to 1:1).
52. 8
53. We thank Professor Weinreb and Dr. Garigipati for helpful discussions concerning this reaction.
54. Similar results were obtained using anhydrous or "wet" TBAF.
55. An excess of reagent (∼3 equiv) was dispensed from a stock solution (1 M in THF). (a) Commercial TBAF (1 M in THF) was from Aldrich Chemical Company (Milwaukee, WI) and was labeled as containing ∼5 wt % water. This reagent was ∼2 years old and had been used successfully to remove TBDMS ethers.
56. (b) Anhydrous TBAF solutions (1 M in THF) prepared from dry TBAF obtained by heating the hydrate in vacuo: Cox, D. P.; Terpinski, J.; Lawrynowicz, W. J. Org. Chem. 1984, 49, 3216.
57. (c) Wet TBAF solutions (1 M in THF) prepared by adding 5% of water (v/v) to an anhydrous solution.
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60. 2,19 (i.e. elimination of the C-5 hydroxy group and intramolecular conjugate addition of the amine nitrogen).
61. 5a
62. 22 total strain energy for 44b and 7 (R = Ms, keto form) (48.9-27.1 = 21.8 kcal/mol) with that for the corresponding diols 44d and 24 (R = Ms, keto form) (40.5-19.1 = 21.4 kcal/mol).
63. 28c "wet" TBAF solutions.
64. 3) and was determined by J modulation.
65. 5d for (±)-isomer.
66. Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392.