Additions and Corrections - The Synthesis of the Optically Active Form of the C-18 Cecropia Juvenile Hormone

1971 ◽  
Vol 93 (20) ◽  
pp. 5315-5315 ◽  
Author(s):  
Peter Loew ◽  
William Johnson
Keyword(s):  
Juvenile Hormone ◽  
Active Form ◽  
Optically Active

Preparation and activity of optically active C16-juvenile hormone

1976 ◽  
Vol 17 (15) ◽  
pp. 1211-1214 ◽  
Author(s):  
Kunio Imai ◽  
Shingo Marumo ◽  
Tetsuya Ohtaki
Keyword(s):  
Juvenile Hormone ◽  
Optically Active

scholarly journals Juvenile hormone activity of optically active ethyl 4-(2-benzylalkyloxy)benzoates inducing precocious metamorphosis

2008 ◽  
Vol 33 (4) ◽  
pp. 383-386 ◽  
Author(s):  
Norihiro Fujita ◽  
Kenjiro Furuta ◽  
Kiyo Ashibe ◽  
Shuhei Yoshida ◽  
Naotaka Yamada ◽  
...  
Keyword(s):  
Juvenile Hormone ◽  
Optically Active ◽  
Hormone Activity ◽  
Juvenile Hormone Activity

Isolation, structure, and synthesis of chenopodanol and the absolute configuration of chenopodene and chenopodanol

1997 ◽  
Vol 75 (6) ◽  
pp. 634-640 ◽  
Author(s):  
Motoo Tori ◽  
Tomonobu Hamaguchi ◽  
Mamiko Aoki ◽  
Masakazu Sono ◽  
Yoshinori Asakawa
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
Active Form ◽  
Optically Active ◽  
Spectroscopic Techniques ◽  
The Absolute

(−)-Chenopodanol (2) has been isolated from the liverwort Marchantiachenopoda and its structure determined by spectroscopic techniques as well as by total synthesis. Chenopodene (1) has also been synthesized in an optically active form, resulting in revision of the originally assigned absolute configuration. Keywords: chenopodanol, chenopodene, liverwort, Marchantiachenopoda, sesquiterpene.

BIOCHEMISTRY OF THE USTILAGINALES: VIII. THE STRUCTURES AND CONFIGURATIONS OF THE USTILIC ACIDS

1953 ◽  
Vol 31 (4) ◽  
pp. 396-417 ◽  
Author(s):  
R. U. Lemieux
Keyword(s):  
Methyl Esters ◽  
Active Form ◽  
Aluminum Hydride ◽  
Optically Active ◽  
Lithium Aluminum ◽  
Acid Oxidation ◽  
Chromic Acid Oxidation ◽  
Pure Compounds ◽  
Hydrolysis Of ◽  
Derivatives Of

Methanolysis of ustilagic acid and hydrolysis of the methyl esters formed yielded a crystalline acidic fraction which was essentially a mixture of two substances termed the ustilic acids A and B. The acids were separated as their iso-propylidene derivatives. The ustilic acids cocrystallize to mixtures with melting points intermediate between those of the pure compounds. Conversion of ustilic acid A, m.p. 112–113 °C, [α]D −8° in methanol, which made up about 70% of the mixture, by hydrogenolysis to palmitic acid, by oxidation with chromic oxide to pentadecanedioic acid, and by lead tetraacetate oxidation followed by hydrogenation to 15-hydroxypentadecanoic acid showed the substance to be an optically active form of 15,16-dihydroxyhexadecanoic acid. Conversion of ustilic acid B, m.p. 140–141 °C, [α]D−10° in methanol, by sodium bismuthate oxidation followed by hydrogenation to 1,14-dihydroxytetradecane, by chromic acid oxidation of its methyl ester followed by hydrolysis of the product, and peroxide oxidation of the α-keto acid thus formed to tetradecanedioic acid, and by hydrogenolysis of the C2-carbon atom through a series of reactions to ustilic acid A, showed the substance to be an optically active form of 2,15,16-trihydroxy-hexadecanoic acid. Optically active forms of 2,15-dihydroxypentadecanoic and 2-hydroxypentadecanoic acids were prepared from ustilic acid B. Application of certain empirical rules of rotation to derivatives of these 2-hydroxyacids showed them to possess the D-configuration. Reduction of ustilic acid B with lithium aluminum hydride gave meso-1,2,15,16-tetrahydroxyhexadecane. Thus, ustilic acid B was the 2D,15D,16-trihydroxyhexadecanoic acid and the ustilic acid A was the 15D,16-dihydroxyhexadecanoic acid. Several derivatives of the above described acids were prepared.

Sign in / Sign up

Export Citation Format

Share Document