Synthesis and absolute configuration of (-)-rothrockene, a non-head-to-tail monoterpene

MR Barbachyn, CR Johnson…

Index: Barbachyn, Michael R.; Johnson, Carl R.; Glick, Milton D. Journal of Organic Chemistry, 1984 , vol. 49, p. 2746 - 2748

Full Text: HTML

Citation Number: 19

Abstract

The total synthesis of (-)-rothrockene, trans-1-(l-methylethenyl)-2-(2~ methyl-l-propenyl) cyclopropane, and ita enantiomer is described. Utilization of (-)-(R)-N, S-dimethyl-S- phenylsulfoximine in the synthesis allowed for resolution of a precursor, regio-and diastereoface selectivity in a Simmons-Smith cyclopropanation, determination of absolute configurations based on X-ray crystallography, and introduction of a side-chain double ...

Related Articles:

Oxidant-free conversion of primary amines to nitriles

[Velcicky, Juraj; Soicke, Arne; Steiner, Roland; Schmalz, Hans-Guenther Journal of the American Chemical Society, 2011 , vol. 133, # 18 p. 6948 - 6951]

Decarboethoxylation of aryl-substituted α-cyanoesters by the method of phase transfer catalysis

[Glushkov; L'vov; Davydova; Kudinova; Polyakova; Sanzharova; Anisimova Pharmaceutical Chemistry Journal, 1997 , vol. 31, # 3 p. 155 - 157]

Electrofluoration en position benzylique dans le sulfolane

[Laurent, Eliane; Marquet, Bernard; Tardivel, Robert Journal of Fluorine Chemistry, 1990 , vol. 49, # 1 p. 115 - 126]

Pd-catalyzed cyanation of benzyl chlorides with nontoxic K 4 [Fe (CN) 6]

[Ren, Yunlai; Yan, Mengjie; Zhao, Shuang; Sun, Yanpei; Wang, Jianji; Yin, Weiping; Liu, Zhifei Tetrahedron Letters, 2011 , vol. 52, # 39 p. 5107 - 5109]

Fluorine-19 substituent chemical shifts (SCS)

[Adcock,W. et al. Australian Journal of Chemistry, 1970 , vol. 23, p. 1921 - 1937]

More Articles...