445289-97-4

Upstream product

• 127793-64-0 (R)-1-O-(tert-butyldiphenylsilyl)-4-penten-1,2-diol 
• 814-68-6 acryloyl chloride 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 2100-17-6 4-pentenal 
• 608130-31-0 (R)-2-(N-phenyl-aminooxy)-pent-4-en-1-ol 
• 107033-46-5 (R)-(tert-butyldiphenylsilyloxy)methyloxirane 

Downstream Products

• 206651-84-5 tert-butyl(((2R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-yl)-methoxy)diphenylsilane 
• 478800-46-3 6-(tert-butyl-diphenyl-silanyloxymethyl)-5,6-dihydro-2H-pyran-2-ol 
• 343981-88-4 tert-butyldiphenyl (((2R,6R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-yl)methoxy)silane 
• 64543-31-3 (-)-5R-5-hydroxydodeca-Z,Z-2,6-dienoic acid lactone 
• 122046-63-3 (6R)-6-[(2S,3S)-3-phenyloxiran-2-yl]-5,6-dihydro-2H-pyran-2-one 
• 22639-28-7 (R)-goniothalamin 
• 206651-83-4 (R)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-5,6-dihydro-2H-pyran-2-one 

Relevant academic research and scientific papers

Stereoselective synthesis of the C1-C12 subunit of (-)-callystatin A

A stereoselective synthesis of the C1-C12 fragment of callystatin A is disclosed. The two stereocenters at C5 and C10 were created by an organocatalytic reaction and a diastereoselective alkylation, respectively. The trisubstituted double bond was introdu

Coibacins a and b: Total synthesis and stereochemical revision

The interface between synthetic organic chemistry and natural products was explored in order to unravel the structure of coibacin A, a metabolite isolated from the marine cyanobacterium cf. Oscillatoria sp. that exhibits selective antileishmanial activity and potent antiinflammatory properties. Our synthetic plan focused on a convergent strategy that allows rapid access to the desired target by coupling of three key fragments involving E-selective Wittig and modified Julia olefinations. CD measurements and comparative HPLC analyses of the natural product and four synthetic stereoisomers led to determination of its absolute configuration, thus correcting the original assignment at C-5 and unambiguously establishing those at C-16 and C-18. Additionally, we synthesized coibacin B on the basis of the assignment of configuration for coibacin A.

An efficient synthesis of synargentolide A from D-mannitol

An efficient synthesis of synargentolide A is described by using d-mannitol and d-malic acid. The key features of the synthetic strategy include Wittig olefination, ring closing-metathesis reaction and cross-metathesis reaction for the formation of synarg

Total synthesis of (R)-(+)-goniothalamin and (R)-(+)-goniothalamin oxide: first application of the sulfoxide-modified Julia olefination in total synthesis

A short and efficient synthesis of (R)-(+)-goniothalamin 1 and (R)-(+)-goniothalamin oxide 2 is described. During this approach, the sulfoxide-modified Julia olefination was used as a key step to connect aldehyde 5 to sulfoxide 6. The desired styryl-containing adduct is obtained in good yield and with excellent E/Z selectivity.

Synthesis of (R)-(-)-argentilactone

A synthesis of (R)-(-)-argentilactone is reported starting from the (S)-enantiomer of glycidol. The synthesis is based on ring closing metathesis of the acrylic ester of (R)-1-O-(tert-butyldiphenylsilyl)-4-penten-1,2-diol 4.