164364-96-9

Upstream product

• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 

Downstream Products

• 164364-98-1 (3S,4R,5R)-2,3-dimethyl-3-(1,3-dioxolan-2-yl)-4-(4-methoxybenzyloxy)-5-(tert-butyldimethylsiloxy)-6-(triisopropylsiloxy)-1-hexene 
• 536737-62-9 (R)-2-[(3R,4R,5R)-2-Methoxy-4-(4-methoxy-benzyloxy)-3-methyl-5-triisopropylsilanyloxymethyl-tetrahydro-furan-3-yl]-propane-1,2-diol 
• 164364-99-2 (2S,3S,4R,5R)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyl-3-(2-propenyl)-5-(triisopropylsiloxymethyl)oxolane 
• 536738-12-2 (2R,3R,4S)-4-[1,3]Dioxolan-2-yl-3-(4-methoxy-benzyloxy)-4,5-dimethyl-hex-5-ene-1,2-diol 
• 536737-61-8 (2S,3S,4R,5R)-5-(hydroxymethyl)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyl-3-(2-propenyl)oxolane 

Relevant academic research and scientific papers

Total synthesis of (+)-asteltoxin

A convergent synthesis of (+)-asteltoxin (1) has been achieved by the Horner-Emmons olefination of bis(tetrahydrofuran) aldehyde 53 and α-pyrone phosphonate 5. A key step features the stereoselective construction of a sterically congested quaternary center embedded in the densely functionalized bis(tetrahydrofuran) subunit by a Lewis acid-catalyzed, pinacol-type rearrangement of an epoxy silyl ether. This pivotal rearrangement methodology parallels the proposed biosynthetic pathway of 1 and is ripe for applications to the stereocontrolled synthesis of structurally complex natural products.