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SEARCH STRING: au:roush and au:riva

  (c) statement:  COPYRIGHT(c) 1997 ACS
         Number:  CAN 108:75079; CAP 1988:75079
      Author(s):  Roush, William R.; Riva, Renata
   Corp. Source:  Dep. Chem., Indiana Univ.; Bloomington, IN 47405, USA
  Article Title:  Enantioselective synthesis of the bottom half of 
                  chlorothricolide.  2.  A comparative study of substituent 
                  effects on the stereoselectivity of the key intramolecular 
                  Diels-Alder reaction
         Source:  J. Org. Chem., 53 (3), 1988, pp. 710-12
          CODEN:  JOCEAH
           ISSN:  0022-3263
       Language:  English
      Pub. Type:  Journal
       Abstract:  The intramol. Diels-Alder reactions of trienes I (R = 
                  SiMe3, Br; R1 = OMe, H) were studied to evaluate the 
                  ability of diene and dienophile substituents to influence 
                  Diels-Alder stereoselectivity and thereby define the 
                  optimal precursor to the bottom half of chlorothricolide.  
                  Ease of prepn. and high yield made I (R = Br, R1 = OMe) 
                  the optimal precursor even though it did not show the 
                  greatest stereoselectivity in the Diels-Alder reaction.
     Keyword(s):  Diels Alder stereochem silyloxytetradecatrienoate 
                  silyloxytetradecatrienal; chlorothricolide 
                  hydroxypropyloctalin fragment
     CA Section:  26 Biomolecules and Their Synthetic Analogs
 Gen Subj Index:  Stereochemistry
                    (of intramol. Diels-Alder reaction of 
                     silyloxytetradecatrienoate and 
                     silyloxytetradecatrienal)
                  Diels-Alder reaction
                    (intramol., of silyloxytetradecatrienoate and 
                     silyloxytetradecatrienal, stereochem. of)
 Chem Sub Index:  
                  1,3-Dioxolane, 2,2-dimethyl-4-[1-(phenylmethoxy)-3-
                   butenyl]-, [R-(R*,S*)]- [87604-53-3]
                    (conversion of, to dibromohexadiene)
                   
                  18H-16a,19-Metheno-16aH-benzo[e]naphtho[2,1-
                   m][1,4]dioxacyclopentadecin-14-carboxylic acid, 
                   1,2,3,4,4a,6a,7,8,9,10,12a,15,16,20,20a,20b-hexadecahydro-
                   4,22-dihydroxy-15,20a-dimethyl-18,20-dioxo-, [4S-
                   (4R*,4aR*,6aS*,11E,12aS*,15S*,16aR*,21aS*,21bS*)]- [41093-
                   63-4]
                    (hydroxypropyloctalin fragment of, stereoselective 
                     prepn. of)
                   
                  Silane, [[6-bromo-8-(phenylmethoxy)-4,6,10-
                   undecatrienyl]oxy](1,1-dimethylethyl)dimethyl-, [S-(Z,E)]-
                    [112505-95-0]
                  Silane, [6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[2-
                   (phenylmethoxy)-4-pentenylidene]-2-hexenyl]trimethyl-, [S-
                   (Z,E)]- [112531-82-5]
                    (prepn. and hydrocyanation of)
                   
                  2,8,10-Tetradecatrienoic acid, 14-[[(1,1-
                   dimethylethyl)dimethylsilyl]oxy]-2-methyl-7-
                   (phenylmethoxy)-9-(trimethylsilyl)-, methyl ester, [S-
                   (Z,E,E)]- [112505-98-3]
                  2,8,10-Tetradecatrienal, 14-[[(1,1-
                   dimethylethyl)dimethylsilyl]oxy]-2-methyl-7-
                   (phenylmethoxy)-9-(trimethylsilyl)-, [S-(Z,E,E)]- [112505-
                   99-4]
                  2,8,10-Tetradecatrienal, 9-bromo-14-[[(1,1-
                   dimethylethyl)dimethylsilyl]oxy]-2-methyl-7-
                   (phenylmethoxy)-, [S-(Z,E,E)]- [112506-00-0]
                  2,8,10-Tetradecatrienoic acid, 9-bromo-14-[[(1,1-
                   dimethylethyl)dimethylsilyl]oxy]-2-methyl-7-
                   (phenylmethoxy)-, methyl ester, [S-(Z,E,E)]- [112531-83-
                   6]
                    (prepn. and intramol. Diels-Alder reaction of, 
                     stereochem. of)
                   
                  Benzene, [[[1-(2,2-dibromoethenyl)-3-butenyl]oxy]methyl]-, 
                   (S)- [112505-92-7]
                    (prepn. and iodosilylation of)
                   
                  Silane, [1-iodo-3-(phenylmethoxy)-1,5-hexadienyl]trimethyl-
                   , [S-(E)]- [112505-93-8]
                    (prepn. and reaction of, with silyloxypentenylboronate)
                   
                  1-Naphthalenecarboxylic acid, 2-[3-[[(1,1-
                   dimethylethyl)dimethylsilyl]oxy]propyl]-1,2,4a,5,6,7,8,8a-
                   octahydro-1-methyl-5-(phenylmethoxy)-4-(trimethylsilyl)-, 
                   methyl ester, [1R-
                   (1.alpha.,2.alpha.,4a.beta.,5.beta.,8a.alpha.)]- [112506-
                   01-1]
                  1-Naphthalenecarboxylic acid, 4-bromo-2-[3-[[(1,1-
                   dimethylethyl)dimethylsilyl]oxy]propyl]-1,2,4a,5,6,7,8,8a-
                   octahydro-1-methyl-5-(phenylmethoxy)-, methyl ester, [1R-
                   (1.alpha.,2.alpha.,4a.beta.,5.beta.,8a.alpha.)]- [112506-
                   02-2]
                  1-Naphthalenecarboxaldehyde, 2-[3-[[(1,1-
                   dimethylethyl)dimethylsilyl]oxy]propyl]-1,2,4a,5,6,7,8,8a-
                   octahydro-1-methyl-5-(phenylmethoxy)-4-(trimethylsilyl)-, 
                   [1R-(1.alpha.,2.alpha.,4a.beta.,5.beta.,8a.alpha.)]- 
                   [112506-03-3]
                  1-Naphthalenecarboxaldehyde, 2-[3-[[(1,1-
                   dimethylethyl)dimethylsilyl]oxy]propyl]-1,2,4a,5,6,7,8,8a-
                   octahydro-1-methyl-5-(phenylmethoxy)-4-(trimethylsilyl)-, 
                   [1S-(1.alpha.,2.beta.,4a.alpha.,5.alpha.,8a.alpha.)]- 
                   [112506-04-4]
                  1-Naphthalenecarboxaldehyde, 4-bromo-2-[3-[[(1,1-
                   dimethylethyl)dimethylsilyl]oxy]propyl]-1,2,4a,5,6,7,8,8a-
                   octahydro-1-methyl-5-(phenylmethoxy)-, [1R-
                   (1.alpha.,2.alpha.,4a.beta.,5.beta.,8a.alpha.)]- [112506-
                   05-5]
                  1-Naphthalenecarboxaldehyde, 2-[3-[[(1,1-
                   dimethylethyl)dimethylsilyl]oxy]propyl]-1,2,4a,5,6,7,8,8a-
                   octahydro-1-methyl-5-(phenylmethoxy)-4-(trimethylsilyl)-, 
                   [1S-(1.alpha.,2.alpha.,4a.beta.,5.alpha.,8a.alpha.)]- 
                   [112531-84-7]
                  1-Naphthalenecarboxylic acid, 2-[3-[[(1,1-
                   dimethylethyl)dimethylsilyl]oxy]propyl]-1,2,4a,5,6,7,8,8a-
                   octahydro-1-methyl-5-(phenylmethoxy)-4-(trimethylsilyl)-, 
                   methyl ester, [1S-
                   (1.alpha.,2.alpha.,4a.beta.,5.alpha.,8a.alpha.)]- [112572-
                   87-9]
                  1-Naphthalenecarboxylic acid, 2-[3-[[(1,1-
                   dimethylethyl)dimethylsilyl]oxy]propyl]-1,2,4a,5,6,7,8,8a-
                   octahydro-1-methyl-5-(phenylmethoxy)-4-(trimethylsilyl)-, 
                   methyl ester, [1S-
                   (1.alpha.,2.beta.,4a.alpha.,5.alpha.,8a.alpha.)]- [112572-
                   88-0]
                  1-Naphthalenecarboxylic acid, 4-bromo-2-[3-[[(1,1-
                   dimethylethyl)dimethylsilyl]oxy]propyl]-1,2,4a,5,6,7,8,8a-
                   octahydro-1-methyl-5-(phenylmethoxy)-, methyl ester, [1S-
                   (1.alpha.,2.alpha.,4a.beta.,5.alpha.,8a.alpha.)]- [112572-
                   89-1]
                  1-Naphthalenecarboxylic acid, 4-bromo-2-[3-[[(1,1-
                   dimethylethyl)dimethylsilyl]oxy]propyl]-1,2,4a,5,6,7,8,8a-
                   octahydro-1-methyl-5-(phenylmethoxy)-, methyl ester, [1S-
                   (1.alpha.,2.beta.,4a.alpha.,5.alpha.,8a.alpha.)]- [112572-
                   90-4]
                  1-Naphthalenecarboxaldehyde, 4-bromo-2-[3-[[(1,1-
                   dimethylethyl)dimethylsilyl]oxy]propyl]-1,2,4a,5,6,7,8,8a-
                   octahydro-1-methyl-5-(phenylmethoxy)-, [1S-
                   (1.alpha.,2.alpha.,4a.beta.,5.alpha.,8a.alpha.)]- [112572-
                   91-5]
                  1-Naphthalenecarboxaldehyde, 4-bromo-2-[3-[[(1,1-
                   dimethylethyl)dimethylsilyl]oxy]propyl]-1,2,4a,5,6,7,8,8a-
                   octahydro-1-methyl-5-(phenylmethoxy)-, [1S-
                   (1.alpha.,2.beta.,4a.alpha.,5.alpha.,8a.alpha.)]- [112572-
                   92-6]
                    (prepn. of, by intramol. Diels-Alder reaction, 
                     stereochem. of)
                   
                  6,8-Dodecadienenitrile, 12-[[(1,1-
                   dimethylethyl)dimethylsilyl]oxy]-5-(phenylmethoxy)-7-
                   (trimethylsilyl)-, [S-(Z,E)]- [112505-96-1]
                  6,8-Dodecadienenitrile, 7-bromo-12-[[(1,1-
                   dimethylethyl)dimethylsilyl]oxy]-5-(phenylmethoxy)-, [S-
                   (Z,E)]- [112505-97-2]
                    (prepn., reductive hydrolysis, and reaction of, with 
                     methoxycarbonylethylidenephosphorane)
                   
                  1,3,2-Benzodioxaborole, 2-[5-[[(1,1-
                   dimethylethyl)dimethylsilyl]oxy]-1-pentenyl]-, (E)- 
                   [112505-94-9]
                    (reaction of, with dibromohexadiene or 
                     iodo(trimethylsilyl)hexadiene)
                   
                  Propanoic acid, 2-(triphenylphosphoranylidene)-, methyl 
                   ester [2605-68-7]
                    (reaction of, with silyloxydodecadienal)

 
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