67680-46-0

Upstream product

• 67680-63-1 Bis-(3,4-dimethoxybenzyloxymethyl)-ether 
• 850146-99-5 3,4-dimethoxybenzyl (methylthio)methyl ether 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 

Downstream Products

• 188359-30-0 (2R,3R)-2-[(1S,2R,5S,6S,7R,8S)-10-Benzenesulfonyl-2-(3,4-dimethoxy-benzyloxymethoxy)-1,5,7-trimethyl-6,8-bis-triethylsilanyloxy-decyl]-5-methoxy-3-methyl-tetrahydro-furan 
• 740836-26-4 (2R,3R)-2-[(1S,2R,5S,6S,8S,9R)-8,10-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxymethoxy)-6-methoxy-1,5,9-trimethyl-decyl]-5-methoxy-3-methyl-tetrahydro-furan 
• 1191041-44-7 C₂₆H₃₃NO₇ 
• 1416510-72-9 Fmoc-(3,4-DMBom)-OH 
• 1416510-82-1 C₁₆H₂₁N₃O₅ 
• 1416510-79-6 C₂₁H₂₉N₃O₇ 
• 850146-93-9 Acrylic acid (E)-(1R,4R,5R,7R)-1-allyl-9-(benzyl-dimethyl-silanyl)-7-(tert-butyl-dimethyl-silanyloxy)-5-(3,4-dimethoxy-benzyloxymethoxy)-4-methyl-4-triethylsilanyloxy-non-2-en-8-ynyl ester 
• 850146-92-8 (E)-(3R,5R,6R,9R)-1-(Benzyl-dimethyl-silanyl)-3-(tert-butyl-dimethyl-silanyloxy)-5-(3,4-dimethoxy-benzyloxymethoxy)-6-methyl-9-triethylsilanyloxy-dodeca-7,11-dien-1-yn-6-ol 
• 850146-94-0 (R)-6-[(E)-(3R,4R,6R)-8-(Benzyl-dimethyl-silanyl)-6-(tert-butyl-dimethyl-silanyloxy)-4-(3,4-dimethoxy-benzyloxymethoxy)-3-methyl-3-triethylsilanyloxy-oct-1-en-7-ynyl]-5,6-dihydro-pyran-2-one 
• 850146-98-4 Acrylic acid (E)-(1R,4R,5R,7R)-1-allyl-9-(benzyl-dimethyl-silanyl)-7-(tert-butyl-dimethyl-silanyloxy)-5-(3,4-dimethoxy-benzyloxymethoxy)-4-hydroxy-4-methyl-non-2-en-8-ynyl ester 
• 850146-97-3 (E)-(4R,7R,8R,10R)-12-(Benzyl-dimethyl-silanyl)-10-(tert-butyl-dimethyl-silanyloxy)-8-(3,4-dimethoxy-benzyloxymethoxy)-7-methyl-dodeca-1,5-dien-11-yne-4,7-diol 
• 1361130-34-8 C₅₅H₇₈O₁₀Si 

Relevant academic research and scientific papers

Second-generation total synthesis of aplyronine A featuring Ni/Cr-mediated coupling reactions

Second-generation total synthesis of aplyronine A, a potent antitumor marine macrolide, was achieved using Ni/Cr-mediated coupling reactions as key steps. The overall yield of the second-generation synthetic pathway of aplyronine A was 1.4%, obtained in 38 steps based on the longest linear sequence. Compared to our first-generation synthetic pathway of aplyronine A, the second-generation synthesis greatly improved both the yield and number of steps. In particular, we improved the stereoselectivity in the construction of the C13 stereogenic center and the C14-C15 (E)-trisubstituted double bond using the asymmetric Ni/Cr-mediated coupling reaction. Furthermore, we established efficient reaction conditions for the asymmetric Ni/Cr-mediated coupling reaction between the C21-C28 segment and C29-C34 segment. Thus, this coupling reaction proceeded with an equimolar ratio of each segment.

Dinuclear asymmetric Zn aldol additions: Formal asymmetric synthesis of fostriecin

Direct asymmetric aldol reactions constitute a powerful methodology for the efficient synthesis of complex natural products. Herein we report the first application of our recently reported dinuclear Zn-catalyzed direct aldol addition of alkynyl ketones to

Aplyronine A, a potent antitumor substance of marine origin, aplyronines B and C, and artificial analogues: Total synthesis and structure-cytotoxicity relationships

The enantioselective total synthesis of aplyronine A (1), a potent antitumor substance of marine origin, was achieved by a convergent approach. Three segments 4, 5, and 6, corresponding to the C5-C11, C21-C27, and C28-C34 portions of aplyronine A (1), were prepared using the Evans aldol reaction and the Sharpless epoxidation as key steps. The coupling reaction of 4 with iodide 7 followed by Julia olefination with sulfone 8 gave the C5-C20 segment 9, while the Julia coupling reaction between segments 5 and 6 provided the C21-C34 segment 10. Julia olefination between segments 9 and 10 and the subsequent four-carbon homologation reaction led to seco acid 83, which was converted into aplyronine A (1) by Yamaguchi lactonization followed by the introduction of two amino acids. The use of the [(3,4-dimethoxybenzyl)oxy]methyl group as a protecting group for the hydroxyl at C29 was crucial for this synthesis. The enantioselective synthesis of two natural congeners, aplyronines B (2) and C (3), was also carried out using the intermediates for the synthesis of 1, which determined the absolute stereostructures of 2 and 3 unambiguously. To study the structure-cytotoxicity relationships of aplyronines, artificial analogues of 1 were synthesized and their cytotoxicities were evaluated: the trimethylserine moiety, two hydroxyl groups, and the side chain portion in 1 turned out to be important in the potent cytotoxicity shown by 1. Biological studies with aplyronine A (1) showed that 1 inhibited polymerization of G-actin to F-actin and depolymerized F-actin to G-actin.