Polymers from a levopimaric acid–acrylic acid Diels–Alder adduct: Synthesis and characterization

2007 ◽  
Vol 45 (24) ◽  
pp. 5979-5990 ◽  
Author(s):  
Ioan Bicu ◽  
Fanica Mustata
Keyword(s):  
Acrylic Acid ◽  
Diels Alder ◽  
Synthesis And Characterization ◽  
Levopimaric Acid ◽  
Alder Adduct

Rearrangements in the Diterpenoid Series. I. The Solvolysis of Methyl 15β-tosyloxy-13-isopropyl-17-noratis-13-en-18-oate

1973 ◽  
Vol 51 (1) ◽  
pp. 77-86 ◽  
Author(s):  
William A. Ayer ◽  
Pandurang D. Deshpande
Keyword(s):  
Diels Alder ◽  
Vinyl Ketone ◽  
Methyl Vinyl Ketone ◽  
Unsaturated Ketone ◽  
Methyl Vinyl ◽  
Levopimaric Acid ◽  
Alder Adduct

The synthesis of methyl 15β-hydroxy-13-isopropyl-17-noratis-13-en-18-oate (14b) is described. Compound 14b was prepared from the ketone 12b, in turn derived from the Diels–Alder adduct formed between levopimaric acid (7) and α-acetoxyacrylonitrile. Solvolysis of the tosylate of 14b proceeds predominantly with rearrangement and elimination to give methyl 16-isopropylidene-7,17-secoacon-8(15)-en-18-oate (16a). This rearrangement serves as a model for the proposed biosynthetic transformation of atisine-type alkaloids into alkaloids of the aconitine series. The degradation of 16a into the unsaturated ketone 19, which contains the 19 carbons of the aconane skeleton, is described. The Diels–Alder addition of methyl vinyl ketone to levopimaric acid is reported and the adduct is shown to possess structure 8.

Synthesis and Characterization of Iso E Super®

2011 ◽  
Vol 396-398 ◽  
pp. 1115-1118 ◽  
Author(s):  
Yue Lin Zhu ◽  
Ji Ne Wang ◽  
Chang Jian Xiong
Keyword(s):  
Industrial Production ◽  
Diels Alder ◽  
Synthesis And Characterization ◽  
Reaction Conditions ◽  
High Yields ◽  
Alder Adduct

A three-step route was used in the study to synthesize the Iso E Super®. Firstly, acetaldehyde was reacted with butanone to obtain 3-methyl-3pentene-2-one, which, in turn, was reacted with myrcene to form a subsitiuted acyl cyclohexene. Finally, the so called Diels-Alder adduct was cyclized. The structure of the products was confirmed by NMR, IR, GC-MS and Roman analysis. The method used has the advantages of readily availability of starting materials, mild reaction conditions, convenient manipulation and moderately high yields, so it has a promising prospect in industrial production

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