159213-03-3

Usage

InChI:InChI=1/C13H19NO2/c1-4-12(15)14(3)10(2)13(16)11-8-6-5-7-9-11/h5-10,13,16H,4H2,1-3H3/t10-,13+/m0/s1

Upstream product

• 90-82-4 pseudoephedrine 
• 123-62-6 propionic acid anhydride 
• 554-12-1 propanoic acid methyl ester 
• 79-03-8 propionyl chloride 

Downstream Products

• 159345-07-0 (2R)-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N,2-dimethylhexanamide 
• 159345-06-9 (2R)-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N,2-dimethyl-3-phenylpropionamide 
• 116060-83-4 (3S,5R)-5-Benzyloxymethyl-3-methyl-dihydro-furan-2-one 

Relevant academic research and scientific papers

Enantioselective synthesis and determination of the absolute configuration of the male sex pheromone of the parasitoid wasp: Urolepis rufipes

Males of the parasitoid wasp Urolepis rufipes use 2,6-dimethyl-7-octene-1,6-diol as a sex pheromone to attract virgin females. Herein, we determine the absolute configuration of the pheromone to be (2S,6S)-2,6-dimethyl-7-octene-1,6-diol (2S,6S-6) and present a stereoselective synthesis of the natural enantiomer of this new linalool derivative. In addition, we show that female wasps respond to the natural 2S,6S-6 stereoisomer while 2R,6S-6 is behaviorally inactive.

Structure-Elucidating Total Synthesis of the (Polyenoyl)tetramic Acid Militarinone C §

The (polyenoyl)tetramic acid militarinone C (1) heads a family of seven members. Before our work, the configuration of C-5 was unknown whereas the configurations of C-8′ and C-10′ were either (R,R) or (S,S). We synthesized the four stereoisomers of constitution 1, which conform with these insights. This included cross-coupling both enantiomers of the western building block (8) with both enantiomers of the eastern building block (9). The specific rotations of the resulting 1 isomers suggested that natural 1 is configured like the coupling partners (S)-8 and (R,R)-9. This conclusion was corroborated by degrading natural 1 to alcohol 35 and by proving its configurational identity with synthetic (R,R)-35.

Enyne metathesis approach towards the cyclopentane motif of jatrophane diterpenes

A short and efficient synthesis of the cyclopentane moiety of the jatrophane diterpene Pl-3 has been developed. The route features an enyne metathesis reaction, and a stereoselective palladium-catalyzed reductive epoxide opening as key steps. Georg Thieme Verlag Stuttgart New York.

Synthesis of methyl N-Boc-(2 S,4 R)-4-methylpipecolate

An efficient stereoselective synthesis of fully protected (2S,4R)-4-methylpipecolic acid has been developed. The synthesis was achieved by initial asymmetric α-alkylation of glycine with a chiral iodide, affording the linear precursor as a single stereoisomer. Subsequent aldehyde formation using OsO4/NaIO4 followed by immediate intramolecular cyclization afforded an enamine that was then subjected to hydrogenation to give the final compound in 23% yield over 10 steps.

General synthesis of highly functionalized cyclopentane segments for the preparation of jatrophane diterpenes

Short and efficient syntheses of two diastereomeric cyclopentane segments present in most jatrophane diterpenes were achieved. Key steps are a stereoselective C-2 elongation, an RCM, and a hydroboration reaction. An orthogonal protecting group methodology

Synthesis of enantiopure bicyclic α,α-disubstituted spirolactams via asymmetric Birch reductive alkylation

The synthesis of enantiopure bicyclic α,α-disubstituted spirolactams is described using a diastereoselective Birch reductive alkylation as the key step. Hydrogenation of the resultant alkylated cyclohexadienes followed by intramolecular cyclization provides access to enantiopure 8-azaspiro[5.6]dodecan-7-ones.

Total synthesis of tubulysin U and V

Multicomponent method: Tubulysins are among the most potent cytotoxic agents known. Now the first total synthesis of some members has been achieved by utilizing a rapid three-component reaction for the synthesis of the unusual central thiazole amino acid

(+)-Sorangicin A synthetic studies. Construction of the C(1-15) and C(16-29) subtargets

(Chemical Equation Presented) Effective stereocontrolled syntheses of subtargets (-)-2 and (-)-4, comprising respectively the C(16-29) and C(1-15) tetrahydropyran and dihydropyran moieties of the potent antibiotic (+)-sorangicin A (1), have been achieved. The cornerstone for the synthesis of (-)-2 involved an aldol tactic exploiting 1,4-induction, followed in turn by an acid-mediated cyclization/ketalization and hydrosilane reduction promoted by TMSOTf, while construction of (-)-4 entailed a stereoselective conjugate addition/α-oxygenation sequence.

Estrogen receptor subtype-selective ligands: Asymmetric synthesis and biological evaluation of cis- and trans-5,11-dialkyl-5,6,11,12- tetrahydrochrysenes

We have recently reported that racemic 5,11-cis-diethyl-5,6,11,12- tetrahydrochrysene-2,8-diol (THC, rac-2b) acts as an agonist on estrogen receptor alpha (ERα) and as a complete antagonist on estrogen receptor beta (ERβ) (Sun et al. Endocrinology 1999, 1