64275-73-6Relevant articles and documents
Preparation of stereochemically pure E- and Z-alkenoic acids and their methyl esters from bicyclo[n.1.0]alkan-1-ols. Application in the synthesis of insect pheromones
Zubrytski,Kananovich,Matiushenkov
, p. 813 - 823 (2017/08/02)
Oxidative cleavage of exo- and endo-alkyl- and hydroxyalkyl-substituted bicyclo[n.1.0]alkan-1-ols with (diacetoxy-λ3-iodanyl)benzene gave the corresponding methyl alkenoates exclusively with E or Z configuration of the double bond. This reaction was used as the key stage in the syntheses of stereoisomerically pure components of pest insect pheromones: (E)-dodec-9-en-1-yl acetate (European pine shoot moth Rhyacionia buoliana), (Z)-tetradec-11-en-1-yl acetate (European oak leafroller Tortrix viridana), and (3E,8Z,11Z)-tetradeca-3,8,11-trien-1-yl acetate (tomato leafminer Tuta absoluta).
Studies on difficult intramolecular hydroaminations in the context of four syntheses of alkaloid natural products
Dion, Isabelle,Vincent-Rocan, Jean-Francois,Zhang, Lei,Cebrowski, Pamela H.,Lebrun, Marie-Eve,Pfeiffer, Jennifer Y.,Bedard, Anne-Catherine,Beauchemin, Andre M.
, p. 12735 - 12749 (2014/01/17)
Examples of intramolecular alkene hydroaminations forming six-membered ring systems are rare, especially for systems in which the double bond is disubstituted. Such cyclizations have important synthetic relevance. Herein we report a systematic study of these cyclizations using recently developed Cope-type hydroamination methodologies. Difficult intramolecular alkene hydroaminations were used as key steps in syntheses of 2-epi-pumiliotoxin C, coniine, N-norreticuline and desbromoarborescidine A. This effort required the development of optimized hydroamination conditions to improve the efficiency of the cyclizations. Collectively, our results show that Cope-type cyclizations can be achieved on a variety of challenging substrates and proceed under similar conditions for both N-H and N-substituted hydroxylamines.
The tandem cope-type hydroamination/[2,3]-rearrangement sequence: A strategy to favor the formation of intermolecular hydroamination products and enable difficult cyclizations
Bourgeois, Joffre,Dion, Isabelle,Cebrowski, Pamela H.,Loiseau, Francis,Bedard, Anne-Catherine,Beauchemin, Andre M.
supporting information; experimental part, p. 874 - 875 (2009/06/19)
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