96947-45-4Relevant academic research and scientific papers
Synthetic studies on the dienophile unit of methyl isosartortuoate. Part 1: Assembly of the acyclic precursor
Hong, Zhangyong,Chen, Xinchao,Xu, Xingxiang
, p. 485 - 488 (2007/10/03)
A strategically functionalized compound, as the acyclic precursor of the dienophile unit of methyl isosartortuoate has been synthesized, and its stereochemistry was also assigned.
Synthesis of hexadeuterated 23-dehydroxybrassinosteroids
Khripach, Vladimir A.,Zhabinskii, Vladimir N.,Antonchick, Andrey P.,Konstantinova, Olga V.,Schneider, Bernd
, p. 1101 - 1108 (2007/10/03)
Two hexadeuterated brassinosteroids (BS) ([26,27-2H6]-23-dehydroxycastasterone and [26,27-2H6]-cathasterone) containing a hydroxy group at C22 instead of the 22R,23R-diol function characteristic for most compounds of this class were prepared for biochemical studies. The corresponding non-deuterated compounds are considered intermediates in brassinolide biosynthesis. The carbon skeleton of the side chain with proper stereochemistry at C24 was prepared from commercially available (2R)-3-hydroxy-2-methylpropanoate. This low molecular fragment was coupled to the tetracyclic steroidal fragment through the reaction of the appropriate sulfone with C22 aldehyde. Formation of the necessary configuration of the 22-hydroxy group was achieved by hydride reduction of the corresponding ketone. Deuterium atoms at C26 and C27 originated from [2H3]methyl iodide used for alkylation of the intermediate sulfone.
Pheromone Synthesis, CXXVI. Synthesis and Biological Activity of Four Stereoisomers of 6,10,14-Trimethyl-2-pentadecanol, the Female-Produced Sex Pheromone of Rice Moth (Corcyra cephalonica)
Mori, Kenji,Harada, Hironori,Zagatti, Pierre,Cork, Alan,Hall, David R.
, p. 259 - 267 (2007/10/02)
The synthesis of four stereoisomers of the female-produced sex pheromone of the rice moth (Corcyra cephalonica) was achieved by starting from (R)-2a, (R)- or (S)-3a, and (R)- or (S)-4 and using alkylation of alkyl phenyl sulfones as the coupling reaction.Behavioral bioassy of each isomer revealed (2R,6R,10R)-1a to be eight times more active than a diastereomeric mixture of equal amounts of the eight possible stereoisomers, indicating that (2R,6R,10R)-1a is probably the natural pheromone or at least themajor component of the female blend.Electrophysiological bioassy also confirmed the high activity of (2R,6R,10R)-1a.
THE TOTAL SYNTHESIS OF 10-(R,S)-C30 BOTRYOCOCCENE AND BOTRYOCOCCANE AND A NEW SYNTHESIS OF A GENERAL INTERMEDIATE TO THE BOTRYOCOCCENE FAMILY.
Hird, Nicholas W.,Lee, Thomas V.,Leigh, Alistair J.,Maxwell, James R.,Peakman, Torren M.
, p. 4867 - 4870 (2007/10/02)
The first synthesis of a C-30 botryococcene has been achieved by using a modified Julia reaction for the key coupling of fragments (2) and (3).The same strategy has been used in a new synthesis of a known synthetic precursor to the entire botryococcene family.
SYNTHESIS OF THE ENANTIOMERS OF CIS-2-METHYL-5-HEXANOLIDE, THE MAJOR COMPONENT OF THE SEX PHEROMONE OF THE CARPENTER BEE
Mori, Kenji,Senda, Shuji
, p. 541 - 546 (2007/10/02)
(2R,5S)-2-Methyl-5-hexanolide and its antipode were synthesized in highly optically pure state (98-99percent e.e.) starting from ethyl (S)-lactate and the enantiomers of methyl β-hydroxyisobutyrate.The specific rotations of our samples were D +/- 91.0 -93.5 deg (CHCl3), while the reported values of the samples prepared by resolution or asymmetric synthesis were +/- 64.5-65.6 deg.
