217486-38-9

Upstream product

• 40411-90-3 Diphenylsulfoniummethylid 
• 217486-32-3 (2R,3R)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-carbaldehyde 
• 217486-62-9 [(2R,3S)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-ylmethoxy]-tert-butyl-dimethyl-silane 
• 217486-29-8 Acetic acid (2R,3S)-9-benzyloxy-3-(tert-butyl-dimethyl-silanyloxymethyl)-6,7-dimethoxy-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-4-yl ester 
• 217486-67-4 [(2R,3S)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-methanol 
• 70775-39-2 dimethylsulfoxonium methylide 
• 30004-64-9 (dimethylamino)phenyloxosulfonium methylide 
• 6814-64-8 methylenedimethyl sulfurane 

Downstream Products

• 217486-64-1 (E)-(R)-1-[(2R,3S)-9-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6,7-dimethoxy-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pent-3-en-1-ol 
• 217486-57-2 (Z)-(R)-1-[(2R,3S)-9-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6,7-dimethoxy-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pent-3-en-1-ol 
• 217486-69-6 (R)-1-[(2R,3S)-9-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6,7-dimethoxy-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-5-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-pent-3-en-1-ol 
• 217486-45-8 (R)-1-[(2R,3S)-9-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6,7-dimethoxy-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-4-methyl-pent-3-en-1-ol 
• 217486-75-4 (2R,3S)-9-Benzyloxy-3-((R)-1-hydroxy-4-methyl-pent-3-enyl)-6,7-dimethoxy-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-4-ol 
• 125224-54-6 furaquinocin B 
• 125108-66-9 furaquinocin A 
• 134984-99-9 furaquinocin D 
• 217486-63-0 (E)-(R)-1-[(2R,3S)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pent-3-en-1-ol 
• 217486-55-0 (Z)-(R)-1-[(2R,3S)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pent-3-en-1-ol 
• 217486-68-5 (R)-1-[(2R,3S)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-3-(2,2-dimethyl-[1,3]dioxan-5-ylidene)-propan-1-ol 
• 217486-42-5 (R)-1-[(2R,3S)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-4-methyl-pent-3-en-1-ol 

Relevant academic research and scientific papers

Implication and improvement of stereoselective methylenation of a chiral aldehyde related to total synthesis of the furaquinocins

In relation to the total synthesis of the furaquinocins, stereoselective methylenation of chiral aldehyde 5 is described. The diastereoselectivity of epoxides 6a/b is high when stabilized sulfur ylides are employed. A double stereo-differentiation phenomenon was observed for the aminosulfoxonium ylide 8: the selectivity with (S)-8 was 30:1, while 5:1 with (R)-8.

Total synthesis of the furaquinocins

A viable synthetic route to the furaquinocin-class antibiotics is described. The key steps include (1) Co-complex mediated stereospecific 1,2- shift of an alkynyl group (9 → 6) to establish the c(2)-C(3) stereochemical relationship, (2) efficient construc