ChemInform Abstract: METAL-ASSISTED TERPENOID SYNTHESIS. IV. NICKEL-CATALYZED REACTIONS OF 1,3-DIENES WITH KETONES. A NEW SYNTHESIS OF LONG CHAIN TERTIARY ALCOHOLS

1977 ◽  
Vol 8 (13) ◽  
pp. no-no
Author(s):  
S. AKUTAGAWA
Keyword(s):  
Tertiary Alcohols ◽  
New Synthesis ◽  
Catalyzed Reactions ◽  
Long Chain

scholarly journals Acid Catalyzed Reactions of alpha-Allenic and alpha-Acetylenic Tertiary Alcohols.

1973 ◽  
Vol 27 ◽  
pp. 1629-1636 ◽  
Author(s):  
Lars-Inge Olsson ◽  
Alf Claesson ◽  
Conny Bogentoft ◽  
Gábor Merényi ◽  
Marcel G. van der Hoeven ◽  
...  
Keyword(s):  
Tertiary Alcohols ◽  
Acid Catalyzed ◽  
Catalyzed Reactions

ChemInform Abstract: Palladium-Catalyzed Reactions of Vinyl Bromides with Disubstituted Alkynes: A New Synthesis of Fulvenes.

ChemInform ◽  
2010 ◽  
Vol 22 (34) ◽  
pp. no-no
Author(s):  
L. J. SILVERBERG ◽  
G. WU ◽  
A. L. RHEINGOLD ◽  
R. F. HECK
Keyword(s):  
New Synthesis ◽  
Palladium Catalyzed ◽  
Catalyzed Reactions

scholarly journals A practical synthesis of long-chain iso-fatty acids (iso-C12–C19) and related natural products

2013 ◽  
Vol 9 ◽  
pp. 1807-1812 ◽  
Author(s):  
Mark B Richardson ◽  
Spencer J Williams
Keyword(s):  
Fatty Acids ◽  
Natural Products ◽  
Selective Reduction ◽  
Isopropyl Group ◽  
Tertiary Alcohols ◽  
Practical Synthesis ◽  
Long Chain

A gram-scale synthesis of terminally-branched iso-fatty acids (iso-C12–C19) was developed commencing with methyl undec-10-enoate (methyl undecylenate) (for iso-C12–C14) or the C15and C16lactones pentadecanolide (for iso-C15–C17) and hexadecanolide (for iso-C18–C19). Central to the approaches outlined is the two-step construction of the terminal isopropyl group through addition of methylmagnesium bromide to the ester/lactones and selective reduction of the resulting tertiary alcohols. Thus, the C12, C17and C18iso-fatty acids were obtained in three steps from commercially-available starting materials, and the remaining C13–C16and C19iso-fatty acids were prepared by homologation or recursive dehomologations of these fatty acids or through intercepting appropriate intermediates. Highlighting the synthetic potential of the iso-fatty acids and various intermediates prepared herein, we describe the synthesis of the natural products (S)-2,15-dimethylpalmitic acid, (S)-2-hydroxy-15-methylpalmitic acid, and 2-oxo-14-methylpentadecane.

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