Pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione ethylene acetal

2005 ◽  
Vol 62 (1) ◽  
pp. o268-o270 ◽  
Author(s):  
Hendrik G. Kruger ◽  
Melanie Rademeyer ◽  
Reshika Ramdhani
Keyword(s):  
Ethylene Acetal

Synthesis and characterization of some oxidized derivatives of citronellal ethylene acetal

1982 ◽  
Vol 60 (14) ◽  
pp. 1847-1852 ◽  
Author(s):  
Wesley G. Taylor
Keyword(s):  
Manganese Dioxide ◽  
Acid Methyl Ester ◽  
Selenium Dioxide ◽  
Glass Capillary Column ◽  
Resonance Spectroscopy ◽  
Glass Capillary ◽  
Geometrical Isomers ◽  
E And Z Isomers ◽  
Ethylene Acetal

Three pairs of geometrical isomers corresponding to allylic monooxidation products of the trisubstituted olefin, citronellal ethylene acetal (3), were synthesized. These compounds were the E and Z isomers of 7-(1,3-dioxolan-2-yl)-2,6-dimethyl-2-hepten-1-ol, -1-al, and -1-oic acid (methyl ester), precursors for identifying the biodegradation products from citronellal and some of its derivatives. The E aldehyde (4) was obtained from 3 by the Sharpless procedure with catalytic quantities of selenium dioxide. The E ester (5) and E alcohol (6) were prepared in high isomeric purity (97–99%) from 4 with activated manganese dioxide and sodium borohydride, respectively. Selective ozonolysis of the isobutenyl group in 3 gave 5-(1,3-dioxolan-2-yl)-4-methyl-1-pentanal (7). Under the conditions used, ozone did not react with the ethylene acetal group. Acetal aldehyde (7) was stereoselectively converted to the Z alcohol (8) by a Wittig reaction. Manganese dioxide oxidation of 8 (98–99% Z isomer) to the Z aldehyde (9) and of 9 to the Z ester (10) was accompanied by partial Z to E isomerization. The distribution of E and Z isomers in crude reaction mixtures was determined by gas chromatography with a glass capillary column or by proton magnetic resonance spectroscopy.

Stereospecific Synthesis of (-)-allo-Muscarine from D-Glucose: Novel Routes to the Key Chiral Synthon

1997 ◽  
Vol 62 (5) ◽  
pp. 809-815 ◽  
Author(s):  
Velimir Popsavin ◽  
Ostoja Beric ◽  
Mirjana Popsavin ◽  
János Csanádi ◽  
Stevan Lajšic ◽  
...  
Keyword(s):  
Mitsunobu Reaction ◽  
Stereospecific Synthesis ◽  
Novel Synthesis ◽  
Derivatives Of ◽  
Chiral Synthon ◽  
Ethylene Acetal

The key chiral synthon in a novel synthesis of (-)-allo-muscarine from D-glucose has been prepared by three independent routes. The most efficient one includes a four-step conversion via the 4-O-benzoyl derivatives of starting 2,5-anhydro-3,5-di-O-methanesulfonyl-L-idose ethylene acetal (2a) into 2,5-anhydro-3,6-dideoxy-L-lyxo-hexose ethylene acetal (4b). The intermediate 4b was efficiently converted into the chiral synthon 2,5-anhydro-4-O-benzoyl-3,6-dideoxy-L-arabino-hexose (4c) by Mitsunobu reaction.

1,5-Dithiacyclooctane-3,7-dione bis(ethylene acetal)

1981 ◽  
Vol 37 (1) ◽  
pp. 261-263 ◽  
Author(s):  
M. M. Olmstead ◽  
W. K. Musker
Keyword(s):  
Ethylene Acetal

ChemInform Abstract: REGIOSELECTIVE REACTIONS OF 2,3-ENDO-EPOXYBICYCLO(3.2.0)HEPTANONE ETHYLENE ACETAL INVOLVING ORGANOMETALLIC REAGENTS

1980 ◽  
Vol 11 (10) ◽  
Author(s):  
R. J. CAVE ◽  
C. C. HOWARD ◽  
G. KLINKERT ◽  
R. F. NEWTON ◽  
D. P. REYNOLDS ◽  
...  
Keyword(s):  
Organometallic Reagents ◽  
Regioselective Reactions ◽  
Ethylene Acetal

Synthesis of allysine ethylene acetal using phenylalanine dehydrogenase from Thermoactinomyces intermedius

2000 ◽  
Vol 26 (5-6) ◽  
pp. 348-358 ◽  
Author(s):  
Ronald L Hanson ◽  
Jeffrey M Howell ◽  
Thomas L LaPorte ◽  
Mary Jo Donovan ◽  
Dana L Cazzulino ◽  
...  
Keyword(s):  
Phenylalanine Dehydrogenase ◽  
Ethylene Acetal
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