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Synthesis of Novel Basic Skeletons Derived from Naltrexone

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Chemistry of Opioids

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 299))

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Notes

  1. 1.

    Although morphine is a classical μ opioid receptor agonist, its intrinsic activity is known to be lower than that of a representative full μ opioid receptor agonist, DAMGO. Moreover, recent reports showed that morphine was a partial agonist for the opioid μ receptor in some pharmacological assays. See [34–38].

  2. 2.

    The thermal decarboxylation of a β-lactone has been widely used for preparation of an olefin. See [51, 52]. Recent examples of the thermal decarboxylation of β-lactones are described in [53–57].

  3. 3.

    Olefins have been prepared by elimination reactions, in which oxazolidinone functioned as a leaving group. See [59–61].

  4. 4.

    In cyclic systems, the extent of anti and syn elimination depends on ring size. Cyclohexyl systems have a very strong preference for anti elimination. See [62, 63].

  5. 5.

    The reaction of 58a with the CPM group seemed to proceed most rapidly. This observation might be explained by considering the very stable cyclopropylcabinyl cation (see Sect. 4 and [39–42]).

  6. 6.

    For X-ray crystallography of nonconjugated iminium salts, see [69–71].

  7. 7.

    For X-ray crystallography of conjugated iminium salts, see [72–82].

  8. 8.

    The NBO analysis showed that the optimal bond length of C6–C7 was also 0.007 Å longer than that of the corresponding bond in 68c, with an interaction energy between σ (C6–C7) and π* (N1–C23) of 4.98 kcal/mol. However, in X-ray crystallography, the C6–C7 in 63b showed the same bond length (1.551 Å) as the C13–C12 in 68c. This result suggested that the C5–C6 might also partially participate in the stabilization of the iminium ion.

  9. 9.

    In the case of the Fe(CO)3 complex 64, the reduction was reported to take 20 min (see [84]). On the other hand, the reduction of 63a was completed within 5 min.

  10. 10.

    The reaction of the Fe(CO)3 complex 64 with NaCN was reported to proceed in acetone under reflux for 5 min (see [83]). In contrast, the reaction of 63a was completed at room temperature within 5 min.

  11. 11.

    The fragmentation of a 7-acyl-6,14-endoethenotetrahydrothebaine derivative was also reported. See [99].

  12. 12.

    For synthesis of pentazocine, see [107–111]. For synthesis of (–)-pentazocine with optical resolution, see [112, 113]. For the asymmetric synthesis of (–)-pentazocine, see the asymmetric synthesis of (–)-metazocine (an N-methyl derivative of (–)-pentazocine) has also been reported, [114]; very recently, the asymmetric synthesis of (–)-9-epi-pentazocine was also reported [115]; it has been shown that (–)-pentazocine is more potent than its antipode [116].

Abbreviations

ACE:

1-Chloroethoxycarbonyl

COSY:

Correlation spectroscopy

CPM:

Cyclopropylmethyl

GPCR:

G-protein-coupled receptor

HMBC:

Heteronuclear multiple bond coherence

HSQC:

Heteronuclear single quantum correlation

MVD:

Mouse vas deferens

NBO:

Natural bond orbital

NOE:

Nuclear Overhauser effect

NTI:

Naltrindole

TCE:

1,1,2,2-Tetrachloroethane

Troc:

2,2,2-Trichloroethoxycarbonyl

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Acknowledgments

We acknowledge the Institute of Instrumental Analysis of Kitasato University, School of Pharmacy for its facilities. We also acknowledge the financial support from Grant-in-Aid for Scientific Research and the Uehara Memorial Foundation and the Shorai Foundation for Science and Technology. We reused some content from [16] (Copyright (2006)), [23] (Copyright (2007)), [26] (Copyright (2008)), [43] (Copyright (2008)), [45] (Copyright (2010)), [87] (Copyright (2009)), [92] (Copyright (2009)), and [97] (Copyright (2009)) with permission from the American Chemical Society or Elsevier.

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  1. School of Pharmacy, Kitasato University, 5-9-1, Shirokane, Minato-ku, Tokyo, Japan

    Hiroshi Nagase & Hideaki Fujii

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  1. Hiroshi Nagase
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  1. School of Pharmaceutical Sciences, Dept. Medicinal Chemistry, Kitasato University, Sirokane 5-9-1, Tokyo, 108-8641, Japan

    Hiroshi Nagase

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Nagase, H., Fujii, H. (2010). Synthesis of Novel Basic Skeletons Derived from Naltrexone. In: Nagase, H. (eds) Chemistry of Opioids. Topics in Current Chemistry, vol 299. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2010_75

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