3,4-Dehydro-2-hydroxy-6-(2-phenethyl)tetrahydropyran. 1,3-Acyclic diastereoselection in reaction with MeOH and its application in the synthesis of a racemic mevinolin analog

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry

Volumn 35, Issue 1, 1996, Pages 8-13

  Yadav, Veejendra K ^a   Kapoor, Kamal K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

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EID: 2742573888     PISSN: 03764699     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (29)

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4. For some recent syntheses of the mevinolin analogs in which the octalin unit is substituted by a phenethyl group, see (a) Bonini C, Pucci P & Viggani L, J Org Chem, 56 (1991) 4050. (b) Johnson C R & Senanayake C H, J Org Chem. 54 (1989) 735.
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8. 3 = 390.2193; Obs. m/z = 390.2180.
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10. -1 more stable than the arabino-counterpart and hence predicted preferential formation of the xylo-species.
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12. see pathway 'a' in ref. 7.
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19. For few other 1,3-diastereoselective processes, see: (b) Oishi T & Tadashi N, Synthesis. (1990) 635. (c) Evans D A & Hoveyda A H, J Org Chem, 55 (1990) 5190. (d) Batra M S, Aguilar F J & Brunet E, Tetrahedron, 50 (1994) 8169 and references cited therein.
20. For few other 1,3-diastereoselective processes, see: (b) Oishi T & Tadashi N, Synthesis. (1990) 635. (c) Evans D A & Hoveyda A H, J Org Chem, 55 (1990) 5190. (d) Batra M S, Aguilar F J & Brunet E, Tetrahedron, 50 (1994) 8169 and references cited therein.
21. -1 where the 'A' value is 1.8; see Nasipuri D, in: Stereochemistry of organic compounds, (Wiley Eastern Ltd, New Delhi) 1991, pp 258-259; also Eliel E L in: Stereochemistry of carbon compounds, (Tata McGraw-Hill Publihsing Co Ltd, New Delhi) 1975, p 236.
22. -1 where the 'A' value is 1.8; see Nasipuri D, in: Stereochemistry of organic compounds, (Wiley Eastern Ltd, New Delhi) 1991, pp 258-259; also Eliel E L in: Stereochemistry of carbon compounds, (Tata McGraw-Hill Publihsing Co Ltd, New Delhi) 1975, p 236.
23. 1H NMR spectra of 9a and 9b (400 MHz) were compared against those of 10a and 10b. The spectra of 10a and 10b were kindly provided to us by Prof. Paul A Grieco. Please see: Grieco P A, Lis R, Zelle R E & Finn J, J Am Chem Soc, 108 (1986) 5908.
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26. For computational evidence supporting the importance of noneclipsed geometries in related carbonyl addition see: (b) Anh N T & Eisenstein O, Nouv J Chim, 1 (1977) 61. (c) Paddon-Row M N, Rondan N G & Houk K N, J Am Chem Soc, 104 (1982) 7162. (d) Houk K N, Paddon-Row M N, Rondan N G, Wu Y-D, Brown F K, Spellmeyer D C, Metz J T, Li Y & Loncharich R J, Science, 231 (1986) 1108.
27. For computational evidence supporting the importance of noneclipsed geometries in related carbonyl addition see: (b) Anh N T & Eisenstein O, Nouv J Chim, 1 (1977) 61. (c) Paddon-Row M N, Rondan N G & Houk K N, J Am Chem Soc, 104 (1982) 7162. (d) Houk K N, Paddon-Row M N, Rondan N G, Wu Y-D, Brown F K, Spellmeyer D C, Metz J T, Li Y & Loncharich R J, Science, 231 (1986) 1108.
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