ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Structural Dynamics of Pentadienyl Metal-Compounds Bearing a Terminal Alkyl Substituent: Both ‘Stereoselective’ and ‘Stereodefensive’ Synthesis of a Natural Perfume.The (2Z, 4E)-, (2E, 4Z)- and (2E, 4E)-isomers of 2,4-decadien-1-ol (5) have been obtained with high and predictable stereochemical homogeneity starting from both (Z)- and (E)-1, 4-decadiene. These hydrocarbons were hydroxylated in a reaction sequence consisting of metallation (by means of s-butyllithium or butyllithium/potassium-t-butoxide, giving rise to organometallic intermediates of specific conformation), dimethoxyborylation and oxidation. The different decadienols as well as (2E, 4Z)-2, 4-undecadien-1-ol were converted into the isovalerates, the ester derived from (2E, 4Z)-2, 4-decadien-1-ol being a natural flavor component.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19800630832
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