200335-69-9

Upstream product

• 1227264-43-8 methyl (3S,4S,5R,6R)-3,4,5-tri{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-6-methoxy-1-cyclohexene-1-carboxylate 
• 219655-90-0 (1S,2S,3S,6S)-5-Bromo-6-methoxy-cyclohex-4-ene-1,2,3-triol 
• 219655-94-4 ((1S,6S)-5-Bromo-6-methoxy-cyclohexa-2,4-dienyloxy)-triisopropyl-silane 
• 219655-88-6 (1S,6S)-2-Bromo-6-triisopropylsilanyloxy-cyclohexa-2,4-dienol 
• 67451-62-1 cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene 
• 219655-92-2 (3S,4S,5R,6R)-6-Methoxy-3,4,5-tris-triethylsilanyloxy-cyclohex-1-enecarboxylic acid methyl ester 
• 1365635-93-3 (3aS,6R,7R,7aS)-methyl 6-methoxy-7-(methoxymethoxy)-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate 
• 1353239-97-0 (3aR,4R,7S,7aS)-methyl 4-methoxy-7-(methoxymethoxy)-2,2-di-methyl-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate 
• 1353239-95-8 (3aR,4R,7S,7aS)-methyl 4-hydroxy-7-(methoxymethoxy)-2,2-di-methyl-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate 
• 1353239-94-7 methyl 2-(hydroxy((4R,5S)-5-((S)-1-(methoxymethoxy)allyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)acrylate 
• 1345470-80-5 (3aS,4R,5R,7aS)-methyl 5-methoxy-4-(methoxymethoxy)-3a,4,5,7a-tetrahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-6-carboxylate 
• 1345470-74-7 C₁₈H₃₄O₄Si 
• 1345470-75-8 (3R,4R)-methyl 3-hydroxy-4-(methoxymethoxy)-2-methylene-4-((2S,3S)-3-vinyl-1,4-dioxaspiro[4.5]decan-2-yl)butanoate 
• 1345470-76-9 C₁₄H₂₂O₅ 

Relevant academic research and scientific papers

Stereoselective synthesis of (+)-pericosine B and (+)-pericosine C using ring closing metathesis approach

Stereoselective synthesis of (+)-pericosine B and (+)-pericosine C were achieved from d-ribose using RCM and RCEYM as key steps.

Application of a tandem seleno-michael/aldol reaction in the total syntheses of (+)-Pericosine B, (+)-Pericosine C, (+)-COTC and 7-chloro-analogue of (+)-Gabosine C

Synthesis of (+)-Pericosine B, (+)-Pericosine C, (+)-COTC and a 7-chloro-analogue of (+)-Gabosine C was achieved via tandem seleno-Michael/aldol reactions as key steps. The carbasugar linear precursor was obtained from cheap and readily available D-ribose in 7 steps which included resolution of the D-ribopyranose and the D-ribofuranose forms. Further transformation of the cyclic product involving a regioselective Steglich esterification or methylation of the secondary hydroxyl group gave rise to protected (+)-COTC, (+)-Pericosine B and (+)-Pericosine C. Deprotection of benzyl ethers at ?78 °C gave the titled compounds in satisfactory yields.

Diastereoselective vinylalumination for the synthesis of pericosine A, B and C

The vinylalumination of α-substituted aldehydes gave anti- and syn-adducts with moderate diastereoselectivity. The diastereomeric ratio was inverted by the addition of lithium or sodium perchlorates. Thus, both anti- and syn-adducts were isolated and transformed into the biologically active conduritols, pericosine B and C, respectively. Formal synthesis of pericosine A was achieved with the anti-adduct. The rationales for the different diastereoselectivity are discussed.

Toward synthesis of carbasugars (+)-gabosine C, (+)-COTC, (+)-pericosine B, and (+)-pericosine C

Asymmetric total synthesis of (+)-gabosine C, (+)-pericosine B, and (+)-pericosine C has been reported from readily available d-(-)-isoascorbic acid and d-ribose involving Grubbs ring closing metathesis, Morita-Baylis-Hillman (MBH) reaction, and Luche red

Total synthesis of (+)-pericosine B and (+)-pericosine C and their enantiomers by using the Baylis-Hillman reaction and ring-closing metathesis as key steps

A simple and divergent route for the total synthesis of pericosine B and pericosine C and their enantiomers from d-ribose by using the Baylis-Hillman reaction and ring-closing metathesis reactions as key steps has been described.

Facile carbohydrate-based stereocontrolled divergent synthesis of (+)-pericosines A and B

An isomer-divergent synthesis of naturally occurring pericosines A and B is described starting from a known d-ribose derived ene-diol in 35% and 41% overall yields respectively of which the latter is the best synthetic method reported for pericosine B. Th

Chemoenzymatic synthesis of carbasugars (+)-pericosines A-C from diverse aromatic cis-dihydrodiol precursors

cis-Dihydrocatechols, derived from biological cis-dihydroxylation of methyl benzoate, iodobenzene and benzonitrile, using the microorganism Pseudomonas putida UV4, were converted into pericosines A, C, and B, respectively. This approach constitutes the shortest syntheses, to date, of these important natural products with densely packed functionalities.

The synthesis of (+)-pericosine B

The first synthesis of (+)-pericosine B is described; this takes seven steps and proceeds in 10% overall yield. The key step in our work is a hydrogen-bonding controlled contra-steric dihydroxylation reaction using osmium tetroxide and an amine promoter. The absolute stereochemistry of the natural product was deduced from the known absolute stereochemistry of our starting material and moreover, the relative and absolute stereochemistry of our synthetic material was determined unambiguously from an X-ray crystal structure of an advanced intermediate.