Total synthesis of the antitumor antibiotic (±)-streptonigrin: first- and second-generation routes for de novo pyridine formation using ring-closing metathesis.

Donohoe, TJ; Jones, CR; Kornahrens, AF; Barbosa, LC; Walport, LJ; Tatton, MR; O'Hagan, M; Rathi, AH; Baker, DB

Abstract:

The total synthesis of (±)-streptonigrin, a potent tetracyclic aminoquinoline-5,8-dione antitumor antibiotic that reached phase II clinical trials in the 1970s, is described. Two routes to construct a key pentasubstituted pyridine fragment are depicted, both relying on ring-closing metathesis but differing in the substitution and complexity of the precursor to cyclization. Both routes are short and high yielding, with the second-generation approach ultimately furnishing (±)-streptonigrin in 1...

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APA Style

Donohoe, T. J., Jones, C. R., Kornahrens, A. F., Barbosa, L. C., Walport, L. J., Tatton, M. R., O'Hagan, M., Rathi, A. H., & Baker, D. B. (2013). Total synthesis of the antitumor antibiotic (±)-streptonigrin: first- and second-generation routes for de novo pyridine formation using ring-closing metathesis. The Journal of Organic Chemistry, 78(24), 12338–12350.

MLA Style

Donohoe, T. J., et al. “Total Synthesis of the Antitumor Antibiotic (±)-Streptonigrin: First- and Second-Generation Routes for De Novo Pyridine Formation Using Ring-Closing Metathesis.” The Journal of Organic Chemistry, vol. 78, no. 24, The Journal of organic chemistry, 2013, pp. 12338–50.

Chicago Style

Donohoe, TJ, CR Jones, AF Kornahrens, LC Barbosa, LJ Walport, MR Tatton, M O'Hagan, AH Rathi, and DB Baker. 2013. “Total Synthesis of the Antitumor Antibiotic (±)-Streptonigrin: First- and Second-Generation Routes for De Novo Pyridine Formation Using Ring-Closing Metathesis.” The Journal of Organic Chemistry 78 (24): 12338–50.
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