Tetrahedron

Synthetic studies on homophymine A: Stereoselective synthesis of (2R, 3R, 4R, 6R)-3-hydroxy-2, 4, 6-trimethyloctanoic acid

F Bellotta, MV D'Auria, V Sepe, A Zampella

Index: Bellotta, Filomena; D'Auria, Maria Valeria; Sepe, Valentina; Zampella, Angela Tetrahedron, 2009 , vol. 65, # 18 p. 3659 - 3663

Full Text: HTML

Citation Number: 4

Abstract

An efficient and highly stereocontrolled synthesis of (2R, 3R, 4R, 6R)-3-hydroxy-2, 4, 6- trimethyloctanoic acid, the β-hydroxy acid unit that acylates the N-terminus of homophymine A, has been devised starting from iodoethane and (S, S)-pseudoephedrine propionamide in 9 steps and 36% average overall yield. Comparison of the 1H and 13C NMR and optical rotation data of the resulting β-hydroxy acid with the natural fragment unambiguously ...

Related Articles:

Decadienoates: sex pheromone components of nettle caterpillars Darna trima and D. bradleyi

[Journal of Chemical Ecology, , vol. 26, # 8 p. 1969 - 1981]

Decadienoates: sex pheromone components of nettle caterpillars Darna trima and D. bradleyi

[Journal of Chemical Ecology, , vol. 26, # 8 p. 1969 - 1981]

Pheromone synthesis. Part 243: Synthesis and biological evaluation of (3R, 13R, 1′ S)-1′-ethyl-2′-methylpropyl 3, 13-dimethylpentadecanoate, the major …

[Mori, Kenji; Tashiro, Takuya; Zhao, Boguang; Suckling, David M.; El-Sayed, Ashraf M. Tetrahedron, 2010 , vol. 66, # 14 p. 2642 - 2653]

Directed Orthometalation and the Asymmetric Total Synthesis of N-Deoxymilitarinone A and Torrubiellone B

[Organic Letters, , vol. 16, # 1 p. 26 - 29]

Pheromone synthesis, CXXV. Synthesis of the four possible stereoisomers of 3, 7??dimethylnonadecane, the female sex pheromone of Agromyza frontella Rondani

[Mori, Kenji; Wu, Jiang Liebigs Annalen der Chemie, 1991 , # 3 p. 213 - 217]

More Articles...