A concise construction of an erythrinane skeleton using Mn(III)/Cu(II)-mediated oxidative radical cyclization of α-methylthio amides

Tetrahedron Letters

Volumn 42, Issue 9, 2001, Pages 1729-1732

  Toyao, Atsushi ^a   Chikaoka, Shiho ^a   Takeda, Yoshifumi ^a   Tamura, Osamu ^a   Muraoka, Osamu ^b   Tanabe, Genzoh ^b   Ishibashi, Hiroyuki ^a  

^a KANAZAWA UNIVERSITY   (Japan)

^b KINKI UNIVERSITY   (Japan)

Author keywords

Alkaloids; Copper and compounds; Manganese and compounds; Radical and radical reactions

Indexed keywords

ALKANE; ALPHA METHYLTHIO AMIDE; AMIDE; COPPER ION; ERYTHRINANE; MANGANESE; UNCLASSIFIED DRUG;

AEROBIC METABOLISM; ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0035951920     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)02335-2     Document Type: Article

References (17)

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11. 2 as an additive are required for the efficient formation of radicals I. See: Ref. 3.
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13. For a review of erythrina alkaloids, see: Tsuda, Y.; Sano, T. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1996; Vol. 48, p. 249.
14. -3, respectively.
15. 3 (4 equiv.) alone also gave 5 in 31% yield together with the starting material 4 (51%). However, this reaction required longer reaction time (3 days).
16. 2Ph). This is probably the result that the cationic intermediate of type VIII (or VIII′) decompose under the reaction conditions due to the lack of such nucleophilic aromatic ring in VIII (or VIII′).
17. Zard and his co-workers reported that Ni/AcOH-mediated reductive radical cyclization of N-(cyclohex-1-enyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]trichloroacetamide gave tetrahydroindol-2-one derivative of type 4 (without MeS group) probably via cationic intermediate similar to IV, but afforded no erythrinane derivative. See: Cassayre, J.; Quiclet-Sire, B.; Saunier, J.-B.; Zard, S. Z. Tetrahedron Lett. 1998, 39, 8995.