95337-97-6

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 19098-31-8 (S)-2-(oxiran-2-yl)ethan-1-ol 
• 76282-48-9 (R)-2-(oxiran-2-yl)ethan-1-ol 

Downstream Products

• 272448-33-6 1-(4-methoxy)phenylamino-4-tert-butyldimethylsilyloxy-2-butanol 
• 655245-73-1 N-tert-butyl-2-[4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-butyl]-benzamide 
• 655245-74-2 N-tert-butyl-2-[4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-butyl]-6-methoxy-benzamide 
• 655245-75-3 N-tert-butyl-2-[4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-butyl]-6-methoxy-4-methyl-benzamide 
• 272448-35-8 1-(4-methoxy)phenyl-2-(2-tert-butyldimethylsilyloxy)ethyl-aziridine 
• 95338-06-0 (S)-1,3-pentanediol 3-(R)-α-methoxy-α-trifluoromethylphenylacetate 1-t-butyldimethylsilyl ether 
• 1399799-28-0 (S)-N-(tert-butyl)-2-[4-(tert-butyldimethylsilyloxy)-2-hydroxybutyl]-6-(methoxymethoxy)benzamide 
• 1399799-20-2 (S)-N-(tert-butyl)-3-butyl-6-[4-(tert-butyldimethylsilyloxy)-2-hydroxybutyl]-2-(methoxymethoxy)benzamide 
• 960211-36-3 (S,Z)-5-(but-2-en-1-yl)-2,2,9,9,10,10-hexamethyl-3,3-diphenyl-4,8-dioxa-3,9-disilaundecane 
• 960211-12-5 C₂₁H₃₅ClO₃Si 
• 960211-35-2 (S)-5-(but-2-yn-1-yl)-2,2,9,9,10,10-hexamethyl-3,3-diphenyl-4,8-dioxa-3,9-disilaundecane 
• 1392426-65-1 C₂₄H₃₇F₃O₄Si 
• 1265177-86-3 (1R,6S,E)-6-(tert-butyldimethylsilyloxy)-1-((2R,5R)-5-(2-(tert-butyldimethylsilyloxy)ethyl)tetrahydrofuran-2-yl)-5-methyl-7-methyleneundec-4-en-2-ynyl 4-nitrobenzoate 

Relevant academic research and scientific papers

Stereoselective total synthesis of obolactones and 7′,8′-dihydroobolactones

A concise stereoselective total synthesis of two diastereomeric obolactones and 7′,8′-dihydroobolactones has been achieved using a metal-free catalytic δ-hydroxyalkynone rearrangement, which could provide the required dihydro-γ-pyrone moiety. The desired first stereogenic center was installed through the chiral pool material,l-aspartic acid. Next, the allylation reaction was strategically utilized to provide the requisite olefin bond for the intended ring-closing metathesis, allowing the installation of the remaining dihydro-α-pyrone moiety in the natural products. It also enabled the targeting of both dihydro-α-pyrone diastereomers. Thus, the first stereoselective total synthesis of (+)-7′,8′-dihydroobolactone was accomplished, establishing its structure and absolute configuration.

Total synthesis and confirmation of the absolute stereochemistry of semiviriditoxin, a naphthopyranone metabolite from the fungus Paecilomyces variotii

The first total synthesis of (S)-semiviriditoxin 2 is described. The approach utilizes a tandem Michael-Dieckmann reaction between ortho-toluate 5 and dihydropyran-2-one 6 to construct the naphthopyranone core, the dihydropyran-2-one 6 being prepared from (R)-1,2-epoxy-4-butanol. Spectroscopic comparison of synthetic (S)-semiviriditoxin 2 with (R)-semivioxanthin 3, prepared in four steps from (R)-propylene oxide, confirmed the (S)-stereochemistry of natural semiviriditoxin from Paecilomyces variotii. Crown Copyright

Total synthesis of (+)-kalafungin using a tandem Michael-Dieckmann approach

A stereoselective synthesis of the antibiotic kalafungin 1 is reported. A key step involved the tandem Michael-Dieckmann reaction between methyl 2-methoxy-6-methylbenzoate 11 and the α,β-unsaturated lactone (R)-6-(2-(tert-butyldimethylsilyloxy)ethyl)-4-methoxy-5,6-dihydropyran-2-one 10, which was prepared from (S)-aspartic acid. The C5 alkyl substituent was introduced by the use of methylmagnesium bromide and subsequent stereoselective reduction. A sequence of oxidations followed by acid-catalyzed epimerization delivered (+)-kalafungin 1.

Absolute Stereochemistry of Exogonic Acid

Exogonic acid (2-(carboxymethyl)-7-methyl-1,6-dioxaspirononane), a resin constituent of the Brazilian tree Ipomoea operculata (Martin) is demonstrated to be predominantly the E,E and Z,Z diastereomers, with the 2S,5S,7R and 2S,5R,7R configurations, respectively.Minor amounts of the 2R,5S,7R E,Z and 2R,5R,7R Z,E isomers are also present.These conclusions are based on chiral gas chromatographic analyses of suitable derivatives and enantioselective syntheses employing (S)-1,2-epoxypropane and (2S)-4-oxy>-1,2-epoxybutane as alkylating agents for anions of acetone N,N-dimethylhydrazone.

Total Synthesis of (+)-Latrunculin A, an Ichthyotoxic Metabolite of the Sponge Latrunculia magnifica, and Its C-15 Epimer

Latrunculin A (1), an ichthyotoxic metabolite of the sponge Latrunculia magnifica with potent inhibitory action on microfilament-mediated processes involved in cell division, was synthesized via a convergent approach.Construction of a major segment of the latrunculin backbone was accomplished by means of a three-component coupling of aldehyde 24, β-keto ester 27, and phosphonium salt 26, which established the conjugated E,Z-diene moiety of 31.The thiazolidinone subunit of 1 was elaborated in the form of 39 from L-cysteine and was linked to 35 without nitrogen protection.Final lactonization of 47 was carried out using the Mitsunobu protocol.A parallel sequence employing the epimeric seco acid 48 produced 15-epilatrunculin A.

SYNTHESIS OF ALL OF THE FOUR ENERGETICALLY POSSIBLE STEREOISOMERS OF 7-ETHYL-2-METHYL-1,6-DIOXASPIRODECANE; A PHEROMONE PRODUCED BY BEES PARAVESPURA VULGARIS L. AND ANDRENA HAEMORRHOA F.

All of the four energetically possible stereoisomers of 7-ethyl-2-methyl-1,6-dioxaspirodecane were synthesized starting from ethyl (S)-lactate and dimethyl (S)-malate or methyl (R)-β-hydroxy-valerate employing dianion alkylation as the key-step.