116237-17-3

Upstream product

• 81577-69-7 [2R,4R,5R]-5-hydroxy-2-phenyl-[1,3]dioxane-4-carbaldehyde 
• 116237-15-1 (E)-4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-but-3-enoic acid 
• 910658-46-7 (E)-(5S,6R)-5,6,7-Trihydroxy-hept-2-enoic acid methyl ester 
• 22900-10-3 2-deoxy-D-ribose 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 78606-80-1 5(S), 6(R), 7-trihydroxyheptanoic acid methyl ester 
• 250226-93-8 (E)-4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-but-2-enoic acid methyl ester 
• 186581-53-3 diazomethane 
• 116237-16-2 4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid 

Downstream Products

• 73466-12-3 Leukotriene A₄ methyl ester 
• 73957-99-0 (-)-(S,S-trans)-3-(hydroxymethyl)oxiranebutanoic acid methyl ester 
• 73958-00-6 (5S,6S)-epoxy-10-formyl-(7E,9E)-decadienoic acid methyl ester 
• 441352-22-3 (2S,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-oxepan-3-one 
• 250226-68-7 (2S,3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-oxepan-3-ol 
• 441352-42-7 (2S,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-6,7-dihydro-oxepin-3-one 
• 250226-81-4 [(2R,3R,4R,5S,6S)-4,5-Bis-benzyloxy-2-((6S,7R)-6-benzyloxy-7-benzyloxymethyl-4,5,6,7-tetrahydro-oxepin-2-ylmethyl)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane 
• 441352-37-0 2,2-Dimethyl-propionic acid 2-((2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4,8-tris-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl)-ethyl ester 
• 351186-83-9 2-((2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4,8-Tris-benzyloxy-9-benzyloxymethyl-5a-methoxy-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl)-ethanol 
• 351186-84-0 (2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-2-Allyl-3,4,8-tris-benzyloxy-9-benzyloxymethyl-5a-methoxy-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalene 
• 440333-91-5 4-[(2S,4aR,5aS,8R,9S,10aR,11aS)-8-(4-Methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-3-oxo-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-butyric acid ethyl ester 
• 441352-51-8 2-((2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4,8-Tris-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl)-ethanol 
• 351186-85-1 (2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-2-Allyl-3,4,8-tris-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalene 
• 441352-49-4 (2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-2-Allyl-3,4,8-tris-benzyloxy-9-benzyloxymethyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene 

Relevant academic research and scientific papers

Syntheses of the AB and EFGH ring segments of gambierol

Stereocontrolled syntheses of the AB and EFGH ring systems of gambierol (1) are described. The two key intermediates 3 and 55, representing the AB and EFGH ring frameworks, were prepared from 2-deoxy-D-ribose via linear sequences. Brown's asymmetric allylboration and the intramolecular hetero-Michael reaction were successfully applied to the construction of the A ring moiety. Synthesis of the EFGH ring segment 55 was achieved by the SmI2 mediated reductive cyclization, constructing the EF ring bearing two 1,3-diaxial methyl groups, and the palladium catalyzed coupling of enol triflate and zinc bishomoenolate, making the GH ring moiety. Attempted convergent approaches toward the EFGH ring framework are also described.

A general strategy for the convergent synthesis of fused polycyclic ethers via B-alkyl Suzuki coupling: Synthesis of the ABCD ring fragment of ciguatoxins

A new method for convergent coupling of fused polycyclic ethers has been developed, which relies on B-alkyl Suzuki crosscoupling of lactone-derived enol triflates or phosphates. The strategy was successfully applied to a convergent synthesis of the ABCD r

Synthetic studies towards gambierol. Part 2: Synthesis of the EFGH ring segment

The EFGH ring segment of gambierol was synthesized from 2-deoxy-D-ribose in 40 steps. The present synthesis includes a SmI2-mediated reductive cyclization and a Pd-catalyzed coupling of enol triflate with a zinc bis-homoenolate as key steps.

A general method for convergent synthesis of polycyclic ethers based on Suzuki cross-coupling: Concise synthesis of the ABCD ring system of ciguatoxin

(matrix presented) A general method for convergent assembly of polyether structure has been developed based on palladium(0)-mediated Suzuki cross-coupling reaction of alkylboranes with cyclic ketene acetal phosphates. The present method allowed for coupli