1428979-98-9

Upstream product

• 2985-33-3 monoethyl methylmalonate 

Downstream Products

• 1428980-13-5 (2R,5R)-2-((1,3-dioxolan-2-yl)methyl)-2,4,5-trimethylcycohex-3-en-1-one 
• 1428980-14-6 (1S,2R,5R)-2-((1,3-dioxolan-2-yl)methyl)-1(2-(ethoxycarbonyl)ethynyl)-2,4,5-trimethylcyclohex-3-en-1-ol 
• 1428980-16-8 (5S,6R,9R)-6-((1,3-dioxolan-2-yl)methyl)-4-methoxy-6,8,9-trimethyl-1-oxaspiro[4.5]deca-3,7-dien-2-one 
• 1428980-17-9 (1S,2R,5R)-2-((1,3-dioxolan-2-yl)methyl)-1-((Z)-1-methoxy-2-(ethoxycarbonyl)ethenyl)-2,4,5-trimethylcyclohex-3-en-1-ol 

Relevant academic research and scientific papers

Synthetic studies of the spirocyclic cyclohexene part of versipelostatin, a novel GRP78/Bip molecular chaperone downregulator

The spirocyclic part consisting of an -acylated tetronic acid and a multisubstituted cyclohexene embedded in versipelostatin, a novel GRP78/Bip molecular chaperone downregulator, has been synthesized in enantiomerically pure form. The asymmetric synthesis of the targeted spiro4.5-1-oxa-7-decen-2,4-dione derivative was characterized by (1) stereoselective allylation at the -carbon of methylmalonate diester, in which one carboxylic acid was esterified with a D-glucose-derived chiral template, (2) construction of the tetrasubstituted cyclohexenone substructure by high-yielding ring-closing metathesis and (3) stereoselective construction of the spirocyclic tetronic acid part starting from the cyclohexenone obtained as the ring-closing metathesis product.