1054740-29-2

Upstream product

• 117709-16-7 (2S,3R)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-hexane-1,2-diol 
• 213766-06-4 3-[(4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-propionic acid methyl ester 
• 213766-10-0 3-[(4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-propan-1-ol 
• 213766-02-0 3-((4R,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid methyl ester 
• 213765-97-0 (4R,5S)-2,2-Dimethyl-4-hydroxymethyl-5-((E)-methoxycarbonylethenyl)-1,3-dioxolane 
• 213766-14-4 4-(tert-butyl-dimethyl-silanyloxymethyl)-5-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolane 

Downstream Products

• 213766-34-8 [3-((2S,4R,5S)-5-Allyloxy-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-propoxy]-tert-butyl-diphenyl-silane 
• 213766-29-1 (2S,4R,5S)-4-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-5-methyl-2-phenyl-[1,3]dioxan-5-ol 
• 213766-78-0 (2S,4aS,6S,7R,9aR)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol 
• 213766-72-4 2-[(2S,4aS,6S,7R,9aR)-7-(tert-Butyl-dimethyl-silanyloxy)-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl]-ethanol 
• 213766-83-7 (2S,4aS,6S,9aR)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4a-methyl-2-phenyl-tetrahydro-1,3,5-trioxa-benzocyclohepten-7-one 
• 213766-89-3 (2S,4aS,6R,9aR)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4a-methyl-2-phenyl-tetrahydro-1,3,5-trioxa-benzocyclohepten-7-one 
• 213766-67-7 tert-Butyl-dimethyl-((2S,4aS,6S,7R,9aR)-4a-methyl-2-phenyl-6-vinyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-yloxy)-silane 
• 213766-75-7 (2S,4aS,6S,7R,9aR)-6-(2-Hydroxy-ethyl)-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol 
• 213766-54-2 (2S,4aS,6S,7R,9aR)-4a-Methyl-2-phenyl-6-vinyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol 
• 213766-24-6 (2S,4R,5S)-4-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2-phenyl-[1,3]dioxan-5-ol 

Relevant academic research and scientific papers

Total synthesis and biological evaluation of (+)-gambieric acid A and its analogues

In this study, we report the first total synthesis and complete stereostructure of gambieric acid A, a potent antifungal polycyclic ether metabolite, in detail. The A/B-ring exocyclic enol ether 32 was prepared through a Suzuki-Miyaura coupling of the B-ring vinyl iodide 18 and the alkylborate 33 and subsequent closure of the A-ring by using diastereoselective bromoetherification as the key transformation. Suzuki-Miyaura coupling of 32 with acetate-derived enol phosphate 49, followed by ring-closing metathesis of the derived diene, produced the D-ring. Subsequent closure of the C-ring through a mixed thioacetalization completed the synthesis of the A/BCD-ring fragment 8. The A/BCD- and F′GHIJ-ring fragments (i.e., 8 and 9) were assembled through Suzuki-Miyaura coupling. The C25 stereogenic center was elaborated by exploiting the intrinsic conformational property of the seven-membered F′-ring. After the oxidative cleavage of the F′-ring, the E-ring was formed as a cyclic mixed thioacetal (i.e., 70) and then stereoselectively allylated by using glycosylation chemistry. Ring-closing metathesis of the diene 3 thus obtained closed the F-ring and completed the polycyclic ether skeleton. Finally, the J-ring side chain was introduced by using a Julia-Kocienski olefination in the presence of CeCl3 to complete the total synthesis of gambieric acid A (1), thereby unambiguously establishing its complete stereostructure. The present total synthesis enabled us to evaluate the antifungal and antiproliferative activities of 1 and several synthetic analogues. Copyright

Synthesis of the E ring of gambierol

The synthesis of the E ring of gambierol was achieved from D-ribose via the intramolecular reaction of allylstannane with an aldehyde as a key step. The undesired stereoisomer formed in this reaction was converted to the desired product by using DBU isome