547739-16-2

Upstream product

• 128461-65-4 3-(p-methoxybenzyloxy)propanal 
• 62322-45-6 allyl methoxymethyl ether 
• 135362-69-5 3-(4-methoxybenzyl)oxypropan-1-ol 

Downstream Products

• 547739-22-0 2-(tert-Butyl-dimethyl-silanyloxy)-6-((1E,3E)-penta-1,3-dienyl)-benzoic acid (Z)-(1S,2S)-1-[2-(4-methoxy-benzyloxy)-ethyl]-2-methoxymethoxy-hexa-3,5-dienyl ester 
• 547739-19-5 2-((E)-Buta-1,3-dienyl)-6-(tert-butyl-dimethyl-silanyloxy)-benzoic acid (Z)-(1S,2S)-1-[2-(4-methoxy-benzyloxy)-ethyl]-2-methoxymethoxy-hexa-3,5-dienyl ester 
• 547739-25-3 (9Z,11Z,13E)-(7S,8S)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[2-(4-methoxy-benzyloxy)-ethyl]-8-methoxymethoxy-7,8-dihydro-6-oxa-benzocyclododecen-5-one 
• 547739-18-4 2-((E)-Buta-1,3-dienyl)-6-hydroxy-benzoic acid (Z)-(1S,2S)-1-[2-(4-methoxy-benzyloxy)-ethyl]-2-methoxymethoxy-hexa-3,5-dienyl ester 
• 547739-20-8 2-((E)-Buta-1,3-dienyl)-6-(tert-butyl-dimethyl-silanyloxy)-benzoic acid (4S,5S)-((Z)-4-buta-1,3-dienyl)-[1,3]dioxepan-5-yl ester 
• 1054645-47-4 (2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methoxymethoxy-pentanal 
• 547739-14-0 (Z)-(3S,4S)-1-(4-Methoxy-benzyloxy)-4-methoxymethoxy-octa-5,7-dien-3-ol 

Relevant academic research and scientific papers

Enantiospecific Synthesis and Cytotoxicity Evaluation of Oximidine II Analogues

Analogues of the anticancer natural product oximidine II were prepared and evaluated for cytotoxicity. One analogue of oximidine II that carries a C15 allylic amide side chain as well as two analogues with C15 vinyl sulfone side chains were found to lack cytotoxicity against the cancer cell line SK-Mel-5, thereby confirming the necessity of the C15 enamide side chain of oximidine II for cytotoxicity. Four analogues, designed by comparative molecular similarity index analysis (CoMSIA), that feature a less complex macrolactone scaffold were prepared and tested. The two analogues carrying a C15 vinyl sulfone group and the two analogues with a C15 oximidine II enamide side chain showed weak cytotoxicity against the SK-Mel-5 cell line and other cell lines, indicating that the designed simplified macrocycles cannot replace the oximidine II macrocycle.

Total synthesis of the salicylate enamide macrolide oximidine II

The asymmetric synthesis of the salicylate enamide macrolide oximidine II is reported. The synthesis involves a highly regio- and stereoselective ring-closing metathesis of a bis-diene substrate to construct the macrocyclic triene core. Copper(I)-mediated