291304-23-9

Upstream product

• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 250226-97-2 (2R,4aR,9aS)-2-Phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-one 
• 250226-93-8 (E)-4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-but-2-enoic acid methyl ester 
• 22900-10-3 2-deoxy-D-ribose 
• 116237-17-3 4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester 
• 116237-16-2 4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 910658-46-7 (E)-(5S,6R)-5,6,7-Trihydroxy-hept-2-enoic acid methyl ester 
• 78606-80-1 5(S), 6(R), 7-trihydroxyheptanoic acid methyl ester 

Downstream Products

• 315203-88-4 [(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-((2R,4aR,9aS)-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-6-ylmethyl)-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane 
• 568572-02-1 {(2R,4aR,6S,7R,9aS)-6-[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-(4-methoxy-benzyloxy)-oxepan-2-ylmethyl]-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-yloxy}-triethyl-silane 
• 568572-11-2 C₃₉H₅₇IO₈Si 
• 568572-03-2 (2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-((2R,4aR,6S,7R,9aS)-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl)-oxepan-3-ol 
• 568571-89-1 (2R,4aR,6S,7R,9aS)-6-[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-(4-methoxy-benzyloxy)-oxepan-2-ylmethyl]-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol 
• 568572-10-1 C₃₉H₅₈O₉Si 
• 568571-90-4 (2R,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-((2R,4aR,6S,7R,9aS)-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl)-oxepan-3-one 
• 568572-09-8 C₃₉H₅₆O₉Si 
• 568571-83-5 C₃₉H₅₆O₈Si 
• 850656-83-6 C₃₄H₄₈O₁₃S 
• 568572-00-9 C₃₃H₄₂O₉ 
• 568572-08-7 C₃₀H₄₄O₁₁S 
• 568571-91-5 C₃₄H₄₆O₇S 
• 568571-92-6 C₃₂H₄₂O₇ 

Relevant academic research and scientific papers

Convergent total synthesis of gymnocin-A and evaluation of synthetic analogues

The first total synthesis of gymnocin-A (1), a cytotoxic polycyclic ether isolated from a notorious red tide dinoflagellate, Karenia mikimotoi, has been accomplished. The synthesis relies heavily on the Suzuki-Miyaura cross-coupling-based methodology to assemble the tetradecacyclic polyether skeleton. Convergent union of the GHI (5) and KLMN (6) rings, both of which were prepared from a common intermediate 7, and the subsequent ring closure of the J ring delivered the GHIJKLMN ring. The crucial coupling between the ABCD and FGHIJKLMN ring fragments (3 and 4, respectively) and stereoselective installation of the C17 hydroxyl group, followed by cyclization of the E ring gave rise to the tetradecacyclic polyether skeleton 2. Finally, incorporation of the 2-methyl-2-butenal side chain completed the total synthesis of gymnocin-A. The convergent nature of the synthesis, which employs three fragments of comparable complexity, is well-suited for preparation of various structural analogues of gymnocin-A to explore the structure-activity relationship. The results of preliminary structure-activity relationship studies of several synthetic analogues are also provided.

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 on a marine polyether toxin, gambierol: Stereoselective synthesis of the FGH ring system via B-alkyl Suzuki coupling

A synthetic route to the FGH ring system of gambierol, a marine polyether toxin isolated from the dinoflagellate Gambierdiscus toxicus, has been developed. The present synthesis features B-alkyl Suzuki coupling of the F and H rings, followed by ring-closure of the G ring and stereoselective installation of 1,3-diaxial methyl groups at C21 and C23. (C) 2000 Elsevier Science Ltd.

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