ChemInform Abstract: Synthesis of a Novel Acetylenic Ester, Methyl E-5-Octadecene-7,9- diynoate.

ChemInform ◽  
2010 ◽  
Vol 22 (9) ◽  
pp. no-no
Author(s):  
S. Y. MHASKAR ◽  
G. LAKSHMINARAYANA
Keyword(s):  
Acetylenic Ester

Total synthesis of (±)-9-deoxygoniopypyrone. Application of the iodocyclofunctionalization reaction of bold α-allenic alcohol derivatives

1998 ◽  
Vol 76 (1) ◽  
pp. 94-101 ◽  
Author(s):  
Richard W Friesen ◽  
Suzanne Bissada
Keyword(s):  
Total Synthesis ◽  
Primary Alcohol ◽  
Silyl Ether ◽  
Protecting Group ◽  
Acetylenic Ester ◽  
The Third ◽  
Vicinal Diol ◽  
Epoxide Opening ◽  
Vinyl Iodide ◽  
Acidic Conditions

The synthesis of ( ±)-9-deoxygoniopypyrone (1) from the α-allenic alcohol 5 is described. Iodocyclofunctionaliztion of the N-tosyl carbamate derivative of 5 using I2 and Ag2CO3 provided, in a highly diastereoselective and regioselective fashion, the vinyl iodo syn-vicinal diol 4. Two routes were explored in order to introduce the third stereogenic centre in the molecule. Reductive deiodination of the vinyl iodide and diastereoselective epoxidation of the derived acetonide14 using mCPBA provided a mixture of epoxides 15 and 16 (2:1) in which the desired threo diastereomer predominated. Alternatively, dihydroxylation of acetonide 14 (OsO4, NMO) yielded a mixture of diols 21 and 22 (2:3) which were separated after monosilylation (TBDMSCl) of the primary alcohol. The major silyl ether erythro diastereomer 24 was converted to the desired epoxide 15 by mesylation (MsCl, Et3N) and epoxide formation (TBAF) with inversion of stereochemistry. The minor threo diastereomer 23 was also converted to the desired epoxide 15 (TBAF; ArSO2Cl; NaOMe). Epoxide opening was effected with lithium acetylide and the resulting alkyne 27 was carbonylated (MeLi, ClCO2Me) to afford the α , β-acetylenic ester 28. Semi hydrogenation over Lindlar's catalyst followed by protecting- group removal under acidic conditions provided ( ±)-8-epigoniodiol 30. Finally, conversion of 30 to ( ±)-9-deoxygoniopypyrone 1 was effected under basic conditions (DBU).Key words: ( ±)-9-deoxygoniopypyrone, α-allenic alcohol, iodocyclofunctionalization, syn-diol.

ChemInform Abstract: An Efficient Synthesis of Functionalized Hexahydropyrimidines via the Reaction of N-Formyl Ureas/Thioureas with an Acetylenic Ester in the Presence of an Aryl Phosphine.

ChemInform ◽  
2016 ◽  
Vol 47 (46) ◽  
Author(s):  
Nasim Shams ◽  
Mohammad Hossein Mosslemin ◽  
Afshin Yazdani ◽  
Hossein Anaraki-Ardakani ◽  
Javad Ghane
Keyword(s):  
Efficient Synthesis ◽  
Acetylenic Ester

scholarly journals HEXACARBONYLMOLYBDENUM-INDUCED FORMATION OF PYRIDINES FROM ISOXAZOLES AND ACETYLENIC ESTER

1983 ◽  
Vol 12 (8) ◽  
pp. 1233-1236 ◽  
Author(s):  
Tomoshige Kobayashi ◽  
Makoto Nitta
Keyword(s):  
Acetylenic Ester

Reactions of some 1,3-dipolarophiles with 1,2-dithioles and 1,2,4-dithiazoles

1969 ◽  
Vol 47 (11) ◽  
pp. 2039-2043 ◽  
Author(s):  
J. M. Buchshriber ◽  
D. M. McKinnon ◽  
M. Ahmed
Keyword(s):  
Spectroscopic Properties ◽  
Acetylenic Ester ◽  
Acetylenic Esters

The reactions of 1,2-dithiole-3-thiones and 1,2,4-dithiazole-3-thiones with acetylenic esters provide initial 1,3-dithiole products by 1,3-dipolar additions. 3-Imino-1,2-dithioles react similarly to form thiazoles. Both these initial adducts react further with more acetylenic ester to form spiran type structures. The stereochemistry of these is discussed briefly and applied to their reactivity and spectroscopic properties.

scholarly journals A multi-pronged mechanistic study of the phosphine-mediated conjugate addition of an alcohol to an acetylenic ester

2014 ◽  
Vol 38 (11) ◽  
pp. 5382-5390 ◽  
Author(s):  
Rhonda L. Stoddard ◽  
Jingwei Luo ◽  
Nicole van der Wal ◽  
Natasha F. O'Rourke ◽  
Jeremy E. Wulff ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Electrospray Ionization ◽  
Electrospray Ionization Mass Spectrometry ◽  
Conjugate Addition ◽  
Ionization Mass Spectrometry ◽  
Mechanistic Study ◽  
Ionization Mass ◽  
Acetylenic Ester ◽  
H Nmr

The conjugate addition of an alcohol to a butynoate ester using an organophosphine catalyst was monitored using pressurized sample infusion electrospray ionization mass spectrometry (PSI-ESI-MS), together with 31P and 1H NMR spectroscopy.

Carbon vs. oxygen abstraction in the photochemical reduction of an acetylenic ester

1979 ◽  
Vol 44 (2) ◽  
pp. 193-195 ◽  
Author(s):  
Vernon S. Stubblefield ◽  
Joseph W. Wilson
Keyword(s):  
Acetylenic Ester ◽  
Photochemical Reduction
Sign in / Sign up

Export Citation Format

Share Document