Studies toward the total synthesis of Sch 202596, an antagonist of the galanin receptor subtype GalR1: Synthesis of geodin, the spirocoumaranone subunit of Sch 202596

Tetrahedron Letters

Volumn 41, Issue 4, 2000, Pages 465-469

  Katoh, Tadashi ^a   Ohmori, Osamu ^a  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

Author keywords

Antibiotics; Biomimetic reactions; Coupling reactions; Cyclization; Spiro compounds

Indexed keywords

ALDEHYDE; ALPHA RESORCYLIC ACID; BENZOPHENONE; BROMIDE; GALANIN; GALANIN RECEPTOR; GEODIN; ORCINOL; RECEPTOR BLOCKING AGENT; SCH 202596; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; ASPERGILLUS; BROMINATION; CHEMICAL REACTION; CYCLIZATION; DRUG INDICATION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; FEEDING DISORDER; MYCOSIS; OBESITY; OXIDATION; STRUCTURE ACTIVITY RELATION;

EID: 0034700853     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02005-5     Document Type: Article

References (29)

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2. 1.
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8. Structurally, 1 belongs to the griseofluvin family of compounds. Therefore, the absolute stereochemistry of the spirocoumaranone moiety in 1 was determined by comparing its circular dichroic (CD) spectrum with that of griseofluvin. The relative stereochemistry of the cyclohexene ring of 1 was revealed by analysis of 2D NMR spectra (COSY, NOESY, HETCOR, and HMBC experiments); however, its absolute stereochemistry has not been established.
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11. Related biogenetic-type phenolic coupling reactions for the construction of the spirocoumaranone ring system have been reported, see: (a) Taub, D.; Kuo, C. H.; Slates, H. L.; Wendler, N. L. Tetrahedron 1963, 19, 1-17. (b) Day, A. C.; Nobney, J.; Scott, A. I. J. Chem. Soc. 1961, 4067-4074. (c) Scott, A. I. Proc. Chem. Soc. 1958, 195.
12. Related biogenetic-type phenolic coupling reactions for the construction of the spirocoumaranone ring system have been reported, see: (a) Taub, D.; Kuo, C. H.; Slates, H. L.; Wendler, N. L. Tetrahedron 1963, 19, 1-17. (b) Day, A. C.; Nobney, J.; Scott, A. I. J. Chem. Soc. 1961, 4067-4074. (c) Scott, A. I. Proc. Chem. Soc. 1958, 195.
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26. When the phenol 4 was treated with a hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate), in acetonitrile at ambient temperature according to the method reported by Kita et al., the desired spirocyclization product 2 could also be produced in 40% yield. See: (a) Tamura, Y.; Yakura, T.; Haruta, J.; Kita, Y. J. Org. Chem. 1987, 52, 3927-3930. (b) Kita, Y.; Egi, M.; Takada, T.; Tohma, H. Synthesis 1999, 885-897.
27. When the phenol 4 was treated with a hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate), in acetonitrile at ambient temperature according to the method reported by Kita et al., the desired spirocyclization product 2 could also be produced in 40% yield. See: (a) Tamura, Y.; Yakura, T.; Haruta, J.; Kita, Y. J. Org. Chem. 1987, 52, 3927-3930. (b) Kita, Y.; Egi, M.; Takada, T.; Tohma, H. Synthesis 1999, 885-897.
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