Record from OCLC FirstSearch CA Student Edition Author Search
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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