536738-12-2

Upstream product

• 81997-76-4 (S,E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropionic acid ethyl ester 
• 536737-59-4 (E)-(S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-5-triisopropylsilanyloxy-pent-2-enoic acid ethyl ester 
• 536737-58-3 (E)-(S)-4,5-Dihydroxy-2-methyl-pent-2-enoic acid ethyl ester 
• 164364-95-8 (2S,3S,4R)-2,3-epoxy-4-(tert-butyldimethylsiloxy)-2-methyl-5-(triisopropylsiloxy)-pent-1-ol 
• 164364-96-9 (3RS,4S,5S,6R)-4,5-epoxy-2,4-dimethyl-6-(tert-butyldimethylsiloxy)-7-(triisopropylsiloxy)-3-(trimethylsiloxy)-1-heptene 
• 536737-60-7 (3S,4R,5R)-2,3-dimethyl-3-(1,3-dioxolan-2-yl)-4-hydroxy-5-(tert-butyldimethylsiloxy)-6-(triisopropylsiloxy)-1-hexene-4-ol 
• 536738-10-0 1-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-triisopropylsilanyloxy-ethyl]-2-methyl-oxiranyl}-2-methyl-prop-2-en-1-ol 
• 536738-08-6 (2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-triisopropylsilanyloxy-ethyl]-2-methyl-oxirane-2-carbaldehyde 
• 164364-97-0 (2S,3R,4R)-2-methyl-2-(2-propenyl)-4-O-(tert-butyldimethylsiloxy)-5-O-(triisopropylsiloxy)-3-hydroxy-pentan-1-al 
• 164364-94-7 (E)-(S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-5-triisopropylsilanyloxy-pent-2-en-1-ol 
• 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 

Downstream Products

• 536737-61-8 (2S,3S,4R,5R)-5-(hydroxymethyl)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyl-3-(2-propenyl)oxolane 
• 164364-99-2 (2S,3S,4R,5R)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyl-3-(2-propenyl)-5-(triisopropylsiloxymethyl)oxolane 
• 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 

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.

A formal synthesis of (+)-asteltoxin

An enantioselective synthesis of the higly functionalized bis(tetrahydrofuran) subunit of asteltoxin has been accomplished, in which a sterically congested quaternary center was constructed by the Lewis acid catalyzed rearrangement of epoxy silyl ethers.