164365-01-9

Upstream product

• 536737-71-0 (2R,3R,4S)-3-(4-methoxybenzyloxy)-4-(1,3-dioxolan-2-yl)-4,5-dimethyl-1,2-bis(triisopropylsiloxy)-5(E)-octene 
• 536737-70-9 (2R,3R,4S)-3-hydroxy-4-(1,3-dioxolan-2-yl)-4,5-dimethyl-1,2-bis(triisopropylsiloxy)-5(E)-octene 
• 536737-77-6 (2R,3R,4S)-3-(4-methoxybenzyloxy)-4-(1,3-dioxolan-2-yl)-4,5-dimethyloct-5(E)-en-1,2-diol 
• 536737-72-1 (2S,3S,4S,5R)-5-(hydroxymethyl)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyl-3-[2(E)-penten-2-yl]oxolane 
• 824-94-2 p-methoxybenzyl chloride 
• 536737-73-2 Triisopropyl-[(2R,3R,4S,5S)-5-methoxy-3-(4-methoxy-benzyloxy)-4-methyl-4-((E)-1-methyl-but-1-enyl)-tetrahydro-furan-2-ylmethoxy]-silane 
• 536737-63-0 (2RS,3R,4R,5R)-3-[(2R,3R)-2,3-dihydroxy-2-pentyl]-5-(triisopropylsiloxymethyl)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyloxolane 

Downstream Products

• 536737-82-3 ethyl (1S,3R,4R,5R,6R,7R)-3-{5,6-dimethyl-7-ethyl-6-hydroxy-4-(4-methoxybenzyloxy)-2,8-dioxabicyclo[3.3.0]oct-3-yl}-prop-2-enoate 
• 536738-15-5 Acetic acid (E)-3-[(2R,3R,3aR,4R,5R,6aS)-5-ethyl-4-hydroxy-3-(4-methoxy-benzyloxy)-3a,4-dimethyl-hexahydro-furo[2,3-b]furan-2-yl]-allyl ester 
• 536737-84-5 (1S,3R,4R,5R,6R,7R)-5,6-dimethyl-7-ethyl-3-(3-hydroxyprop-1(E)-enyl)-4-(4-methoxybenzyloxy)-2,8-dioxabicyclo[3.3.0]octan-6-ol 
• 164365-04-2 (2E,4E)-5-[(2R,3R,3aR,4R,5R,6aS)-5-Ethyl-4-hydroxy-3-(4-methoxy-benzyloxy)-3a,4-dimethyl-hexahydro-furo[2,3-b]furan-2-yl]-penta-2,4-dienoic acid ethyl ester 
• 536737-79-8 (2S,3R,3aR,4R,5R,6aR)-5-Ethyl-4-hydroxy-3-(4-methoxy-benzyloxy)-3a,4-dimethyl-hexahydro-furo[2,3-b]furan-2-carbaldehyde 
• 79663-49-3 asteltoxin 
• 164365-02-0 (1S,3R,4R,5R,6R,7R)-5,6-dimethyl-7-ethyl-3-(hydroxymethyl)-4-(4-methoxybenzyloxy)-2,8-dioxabicyclo[3.3.0]octan-6-ol 

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.