46481-05-4

Upstream product

• 616-16-0 (R)-2-Methyl-1-butanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 1068600-85-0 (2R)-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methyl-2-methylbutanamide 
• 474828-48-3 (R)-4-benzyl-3-((R)-2-methylbutanoyl) oxazolidin-2-one 
• 32793-87-6 (R)-1-<(2-methylbutoxy)methyl>benzene 
• 130856-00-7 (R)-2-methyl-1-(2-tetrahydropyranyloxy)butane 
• 69743-62-0 (R)-2-methylbutyl benzoate 
• 69743-61-9 (R)-2-methylbutyl acetate 
• 110595-22-7 (R)-4-acetoxy-3-methyl-1-butene 
• 22644-30-0 (R)-2-methylbut-3-en-1-ol 
• 110659-28-4 (R)-(+)-5-acetoxy-4-methylpentanoic acid 
• 110659-29-5 (R)-2-methyl-3-buten-2-yl tosylate 

Downstream Products

• 36272-22-7 (R)-(+)-2-methylbutylamine 
• 185745-72-6 ((3R,13R)-3,13-Dimethyl-heptadecane-5-sulfonyl)-benzene 
• 185745-74-8 ((3R,13S)-3,13-Dimethyl-heptadecane-5-sulfonyl)-benzene 
• 162610-58-4 (S)-3-benzyloxy-2-hydroxypropyl (R)-12-methyltetradecanoate 
• 1369415-62-2 (R)-(2-methylbutyl)triphenylphosphonium iodide 
• 1159426-59-1 (2R,4R)-N-[(1'S,2'S)-2'-hydroxy-1'-methyl-2'-phenylethyl]-N-methyl-2,4-dimethylhexanamide 
• 250229-74-4 (2R,6R,10R)-1-tert-butyldiphenylsilyloxy-2,6,10-trimethyldodecane 
• 70200-36-1 (R)-3-methylpentan-1-ol tosyl ester 
• 16958-25-1 (R)-3-methylpentanoic acid 
• 75983-36-7 (4RS,8R)-4,8-dimethylacetal 
• 99032-67-4 (S)-(+)-1-bromo-2-methylbutane 
• 114088-42-5 (6R,10R,3RS)-2,3-isopropylidenedioxy-2,6,10-trimethyldodecane 

Relevant academic research and scientific papers

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.

Studies on tridecaptin B1, a lipopeptide with activity against multidrug resistant Gram-negative bacteria

Previously other groups had reported that Paenibacillus polymyxa NRRL B-30507 produces SRCAM 37, a type IIA bacteriocin with antimicrobial activity against Campylobacter jejuni. Genome sequencing and isolation of antimicrobial compounds from this P. polymyxa strain show that the antimicrobial activity is due to polymyxins and tridecaptin B1. The complete structural assignment, synthesis, and antimicrobial profile of tridecaptin B1 is reported, as well as the putative gene cluster responsible for its biosynthesis. This peptide displays strong activity against multidrug resistant Gram-negative bacteria, a finding that is timely to the current problem of antibiotic resistance.

Asymmetric synthesis and absolute configuration of streptophenazine G

The asymmetric synthesis of the antibacterial natural product, streptophenazine G, has been achieved by employing asymmetric alkylation and asymmetric aldol reactions using chiral oxazolidinones as the key steps. The originally proposed structure for streptophenazine G has been revised, and its absolute configuration has been determined to be 1′S,2′R,6′S. The asymmetric total synthesis of 6′-epi-streptophenazine G is also described.

Pheromone synthesis. Part 243: Synthesis and biological evaluation of (3R,13R,1′S)-1′-ethyl-2′-methylpropyl 3,13-dimethylpentadecanoate, the major component of the sex pheromone of Paulownia bagworm, Clania variegata, and its stereoisomers

All of the four stereoisomers of (1′S)-1′-ethyl-2′-methylpropyl 3,13-dimethylpentadecanoate, the major component of the female sex pheromone of Clania variegata, were synthesized by employing olefin cross metathesis as the key reaction and starting from (R)- or (S)-2-methyl-1-butanol, (R)- or (S)-citronellal, and (S)-2-methyl-3-pentanol. Their bioassay revealed the (3R,13R,1′S)-isomer as the bioactive one, whose more efficient synthesis was achieved in two different ways by employing Wittig reaction as the key step.

Pheromone synthesis. Part 240: Cross-metathesis with Grubbs I (but not Grubbs II) catalyst for the synthesis of (R)-trogodermal (14-methyl-8-hexadecenal) to study the optical rotatory powers of compounds with a terminal sec-butyl group

(R)-Trogodermal (14-methyl-8-hexadecenal), the sex pheromone of Trogoderma species of pest insects against stored products, and its (S)-isomer were synthesized by using olefin cross-metathesis between (R)- or (S)-7-methyl-1-nonene and 8-nonenyl acetate as the key step. This step was successful with Grubbs I but not with Grubbs II catalyst. The latter caused randomization of the carbon skeleton to give a mixture of abnormal products with both longer or shorter carbon chains than the desired product. The specific rotations of 18 newly and 6 previously synthesized compounds with a terminal sec-butyl group were measured to conclude them to be [α]D +3.5 to +6.5 or -3.6 to -6.4.

Synthesis of all the four stereoisomers of (1′S)-1-ethyl-2-methylpropyl 3,13-dimethylpentadecanoate, the major component of the sex pheromone of Paulownia bagworm, Clania variegata

All the four stereoisomers of (1′S)-1-ethyl-2-methylpropyl 3,13-dimethylpentadecanoate, the major component of the sex pheromone of Clania variegata, were synthesized by starting from (R)- or (S)-2-methylbutan-1-ol, (R)- or (S)-citronellal, and (S)-2-methylpentan-3-ol. Olefin cross metathesis was employed as the key reaction.

Synthesis and odor evaluation of stereoisomers of imine derivatives in roasted spotted shrimp

All possible stereoisomers of imine derivatives 1-4. which have the characteristic roast odor of seafood, were synthesized. As a result of odor evaluation of all isomers, we found that each isomer has a different and characteristic odor of roasted seafood.

Regio- and stereochemical study of sex pheromone of pine sawfly; Diprion nipponica

Regio- and stereoisomers of 1,2,ω-trimethyldecyl propionate (ω = 5-9) were prepared from stereochemically pure chiral building blocks as sex pheromone candidates of a pine sawfly; Diprion nipponica. Among the synthesized candidates, (1S,2R,8S)-1,2,8-trimethyldecyl propionate was found to be the sex pheromone of D. nipponica, based on compatibility of its GC-MS data with that of the extract of females, and its significantly high pheromone activity in a field bioassay. The field bioassay of the synthesized compounds also revealed that (1S,2R,SR)-1,2,8-trimethyldecyl propionate, (1S,2R,7S)-1,2,7-trimethyldecyl propionate, and (1S,2R,6S)-1,2,6-trimethyldecyl propionate could attract male sawflies to some extent as pheromone mimics.

Pheromone synthesis, CXCVIII. Synthesis of (1S,2S,6S,10R)- and (1S,2R,6R,10R)-1,2,6,10-tetramethyldodecyl propanoate, the components of the sex pheromone of the pine sawfly, Microdiprion pallipes

(1S,2S,6S,10R)- and (1S,2R,6R,10R)-1,2,6,10-tetramethyldodecyl propanoate (1 and 2), the components of the pheromone of Microdiprion pallipes, were synthesized from two chiral and nonracemic building blocks, (R)-3-tert-butoxycarbonyl-2-methylpropanoic acid (D) and (2R,6S)-7-acetoxy- 2,6-dimethyl-1-heptanol (G), by employing lipase-catalyzed kinetic resolution in a later step.

Pheromone Synthesis, CLXXVI: Synthesis of the four stereoisomers of 3,13-dimethylheptadecane, the major sex pheromone component of the western false hemlock looper

All of the four stereoisomers of 3,13-dimethylheptadecane (1), the female-produced sex pheromone of the western false hemlock looper (Nepytia freemani), were synthesized by starting from the enantiomers of citronellol (2a) and 2-methyl-1-butanol (4a). VCH Verlagsgesellschaft mbH, 1996.