61254-17-9

Upstream product

• 58262-61-6 (1R,2S,5S,6S)-4-hydroxy-2,6-bis(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane 
• 120-57-0 piperonal 
• 572916-32-6 (2S,3R,4R)-4-[(S)-(methoxymethoxy)(3,4-methylenedioxyphenyl)methyl]-2-(3,4-methylenedioxyphenyl)-3-tetrahydrofurancarbaldehyde 
• 572916-26-8 (2S,4R)-4-[(R)-(3,4-methylenedioxyphenyl)(triisopropylsilyloxy)methyl]pentane-1,2,5-triol 
• 572916-20-2 (2S,4R)-4-[(S)-(3,4-methylenedioxyphenyl)(triisopropylsilyloxy)methyl]pentane-1,2,5-triol 
• 572916-31-5 (2S,3R,4R)-3-hydroxymethyl-4-[(S)-(methoxymethoxy)(3,4-methylenedioxyphenyl)methyl]-2-(3,4-methylenedioxyphenyl)tetrahydrofuran 
• 572916-24-6 (2R,3R)-2-[(S)-(hydroxy)(3,4-methylenedioxyphenyl)methyl]-3-[(S)-(methoxymethoxy)(3,4-methylenedioxyphenyl)methyl]butane-1,4-diol 
• 572916-30-4 (2R,3R)-2-[(R)-(hydroxy)(3,4-methylenedioxyphenyl)methyl]-3-[(S)-(methoxymethoxy)(3,4-methylenedioxyphenyl)methyl]butane-1,4-diol 
• 572916-25-7 (2S,4S)-2-[(R)-(3,4-methylenedioxyphenyl)(triisopropylsilyloxy)methyl]-5-trityloxy-4-pentanolide 
• 572916-19-9 (2S,4S)-2-[(S)-(3,4-methylenedioxyphenyl)(triisopropylsilyloxy)methyl]-5-trityloxy-4-pentanolide 
• 58262-61-6 4-hydroxysesamin 
• 62848-90-2 trans-4-carboxy-5-(3,4-methylenedioxyphenyl)dihydrofuran-2(3H)-one 
• 16108-37-5 trans-4-hydroxymethyl-5-(3,4-methylenedioxyphenyl)-dihydrofuran-2(3H)-one 
• 105602-56-0 (4S,5R)-5-Benzo[1,3]dioxol-5-yl-4-(benzo[1,3]dioxol-5-yl-methoxy-methoxymethyl)-dihydro-furan-2-one 

Downstream Products

• 133-03-9 rac-(1R,2R,5R,6S)-2,6-bis(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane 

Relevant academic research and scientific papers

Synthesis of (+)-aptosimon, a 4-oxofurofuran lignan, by erythro selective aldol condensation and stereoconvergent cyclization as the key reactions

The 4-oxofurofuran lignan, (+)-aptosimon (1), was synthesized from γ-butyrolactone (9). To construct the two benzylic chiral center of (+)-aptosimon (1), highly erythro selective aldol condensation and stereoconvergent SN1 intramolecular cyclization were used as the key reactions.

C-H insertion approach to the synthesis of endo,exo-furofuranones: Synthesis of (±)-asarinin, (±)-epimagnolin A, and (±)-fargesin

A series of novel 5-aryl-4-aryloxymethyl-3-diazotetrahydrofuran-2-ones (12, 24, and 35a/b) have been prepared and found to undergo regio- and stereoselective C-H insertion reactions to afford 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane-8-ones (18, 26, and 36a/b) with endo,exo stereochemistry. Subsequent reduction of the lactone ring and cyclization of the resulting diols 27 and 37a/b permitted the synthesis of three endo, exo-furofuran lignans: asarinin (2), fargesin (3), and epimagnolin A (4). En route to the key diazo compounds 24 and 35a/b, a modified procedure for the Ghosez keteniminium-olefin cyclization was developed, which was required to minimize the decomposition of acid-sensitive functional groups such as electron-rich benzylic ethers that were present in the target compounds 2-4.

Synthesis of endo,exo-furofuranones using a highly diastereoselective C-H insertion reaction

A highly stereoselective ring closure of α-diazo-γ-butyrolactones to form the 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane ring system is reported; a formal synthesis of the furofuran lignan asarinin 1 is also described.

A New Synthetic Route to Furofuranoid Lignans via Intramolecular Mukaiyama reaction

The sequence set out in Scheme 1 provides a short and expedient synthesis of a number of (+/-)-furofuranoid lignans, including styraxin 3 (antitumor), aptosimon 5, asarinin 6, pluviatilol 7, 'MEL' 4 (inhibitor of germination) and related compounds.

Synthesis and N.m.r. Spectra of 2,6- and 2,4-Diaryl-3,7-dioxabicyclooctanes

A series of isomeric 2,6- and 2,4-diaryl-3,7-dioxabicyclooctanes have been prepared via the corresponding threo, and erythro-dioxo-diesters.Comparison of their 1H and 13C n.m.r. spectra reveals small differences in chemical shifts and coupling constants which could be diagnostic in assigning structures to such compounds.The structure of 4-hydroxysesamin has been confirmed by direct correlation with sesamin.