144398-20-9Relevant academic research and scientific papers
Elaboration of a Baylis-Hillman adduct to (-)-acaterin and its diastereomer through ring closing metathesis
Anand, R.Vijaya,Baktharaman,Singh, Vinod K.
, p. 5393 - 5395 (2002)
A short and efficient synthesis of acaterin, a biologically important natural product has been achieved by elaboration of a Baylis-Hillman adduct. The key step for the synthesis is a ring closing metathesis reaction using Grubbs' catalyst.
Biosynthesis of acaterin: Metabolic fate of sn-3 hydrogens of glycerol during the formation of 4-dehydroacaterin
Sekiyama, Yasuyo,Fujimoto, Yoshinori,Hasumi, Keiji,Endo, Akira
, p. 4223 - 4226 (1999)
The metabolic fate of the pro-R and pro-S hydrogens at the sn-C-3 position of glycerol during the formation of 4-dehydroacaterin has been investigated using Pseudomonas sp. A92. Feeding studies of sn-(3R)- and sn-(3S)-(3-2H)glycerols revealed that 5E hydrogen of 4-dehydroacaterin originates mainly from pro-R hydrogen at sn-C-3 of glycerol, while 5Z hydrogen comes mainly from pro-S. These results ruled out pyruvate and lactate as the immediate precursor of the C3 branched unit of acaterin, and suggest 1,3-bisphosphoglyceric acid or its biological equivalent as the precursor.
Synthesis of all the four possible stereoisomers of acaterin, naturally occurring ACAT inhibitor, and the determination of its absolute configuration
Ishigami, Ken,Kitahara, Takeshi
, p. 6431 - 6442 (1995)
Enantioselective synthesis of all the possible stereoisomers of acaterin 1, naturally occurring ACAT inhibitor with acetogenin-type skeleton, was accomplished starting from both the enantiomers of ethyl 3-hydroxy butanoate 3. Stereochemistry of synthetic samples 1 and pseudo-1 was unambiguously assigned by converting to the authentic compound. The absolute configuration of natural acaterin was determined as (4R, 1'R) by careful comparison of TLC behavior and spectral and optical data.
Tellurium in organic synthesis: A general approach to buteno- and butanolides
Ferrarini, Renan S.,Dos Santos, Alcindo A.,Comasseto, Jo?o V.
, p. 8431 - 8440 (2012/10/07)
The naturally occurring butanolides (-)-blastmycinolactol, (+)-blastmycinone, (-)-NFX-2, (+)-antimycinone as well as the four stereoisomers of the butenolide Acaterin were prepared in high enantiomeric purity using hydroxy-vinyl tellurides as starting mat
Tellurium in organic synthesis: A general approach to buteno- and butanolides
Ferrarini, Renan S.,Dos Santos, Alcindo A.,Comasseto, Joao V.
, p. 10601 - 10610,10 (2012/12/13)
The naturally occurring butanolides (-)-blastmycinolactol, (+)-blastmycinone, (-)-NFX-2, (+)-antimycinone as well as the four stereoisomers of the butenolide Acaterin were prepared in high enantiomeric purity using hydroxy-vinyl tellurides as starting mat
Tellurium in organic synthesis: A general approach to buteno- and butanolides
Ferrarini, Renan S.,Dos Santos, Alcindo A.,Comasseto, Jo?o V.
, p. 10601 - 10610 (2013/01/15)
The naturally occurring butanolides (-)-blastmycinolactol, (+)-blastmycinone, (-)-NFX-2, (+)-antimycinone as well as the four stereoisomers of the butenolide Acaterin were prepared in high enantiomeric purity using hydroxy-vinyl tellurides as starting mat
Asymmetric synthesis of (-)-acaterin
Kandula, Subba Rao V.,Kumar, Pradeep
, p. 6149 - 6151 (2007/10/03)
The asymmetric synthesis of (-)-acaterin, an inhibitor of acyl-CoA cholesterol acyl transferase has been achieved starting from the commercially available starting materials, octan-1-ol and methyl (R)-lactate. The key steps are a Sharpless asymmetric dihydroxylation and a Wittig olefination.
