111187-62-3Relevant articles and documents
Dehydration of hexacarbonyldicobalt protected tertiary propargylic alcohols. Stereo- and regiochemistry, synthesis of enantiomerically pure manicone and normanicone
Melikyan,Mineif,Vostrowsky,Bestmann
, p. 633 - 636 (1991)
The stereochemistry and regiochemistry of the dehydration of hexacarbonyl-μ-[η-(3RS,5S)-(+)-3,5-dimethyl-1-heptyn-3-ol]dicobalt (Co-Co) and hexacarbonyl-μ-[η-(4RS,6S)-(+)-4,6-dimethyl-7-octyn-4-ol]dicobalt (Co-Co) with diethyl ether-boron trifluoride complex, trifluoroacetic acid or phosphorus(V) oxide have been investigated. The distribution of the isomeric products [(E)-enynes 41-86%, (Z)-enynes 9-59%, enynes with exomethylene group 0-9%] is dependent on the substrate structures as well as the nature of dehydrating agent: By acid-catalyzed hydration of the corresponding enynes enantiomerically pure (E,S)-(+)-4,6-dimethyl-4-octen-3-one (manicone) and (E,S)-(+)-3,5-dimethyl-3-hepten-2-one (normanicone) have been synthesized.
A facile one-pot stereoselective synthesis of trisubstituted (E)-2-methylalk-2-enoic acids from unactivated Baylis-Hillman adducts and a simple access to some important insect pheromones
Das, Biswanath,Chowdhury, Nikhil,Banerjee, Joydeep,Majhi, Anjoy
, p. 6615 - 6618 (2007/10/03)
An efficient one-pot stereoselective synthesis of trisubstituted (E)-2-methylalk-2-enoic acids has been accomplished by treatment of unactivated Baylis-Hillman adducts, 3-hydroxy-2-methylenealkanoates, with Al-NiCl2·6H2O in methanol at room temperature followed by hydrolysis. The method has been applied to the synthesis of three important insect pheromones, (4S,2E)-2,4-dimethyl-2-hexenoic acid, (+)-(S)-manicone and (+)-(S)-normanicone.
Pheromones, 65. - Identification of the Volatile Components of the Mandibular Gland Secretion of the Ant Manica rubida: Structure Elucidation, Synthesis, and Absolute Configuration of Manicone
Bestmann, Hans Juergen,Attygalle, Athula B.,Glasbrenner, Juergen,Riemer, Roland,Vostrowsky, Otto,et al.
, p. 55 - 60 (2007/10/02)
By means of gas chromatography and mass spectrometry, manicone, (4E)-4,6-dimethyl-4-octen-3-one (1), was identified as the main component of the mandibular gland secretion of the ant Manica rubida.In addition the presence of homomanicone (2), bishomomanicone (3), normanicone (7), and a few aliphatic aldehydes and ketones was also evident in the gland.Racemic 1, 2, and 7 and optically active dihydromanicone (4), were synthesized.The (S) configuration of 1 was determined by complexation gas chromatography, on a chiral phase, of 4 as well as of the hydrogenation products of racemic and natural 1.
