346584-10-9

Upstream product

• 315204-12-7 tert-Butyl-dimethyl-[(2R,4S,5R)-2-phenyl-4-((2R,3R)-3-vinyl-oxiranylmethyl)-[1,3]dioxan-5-yloxy]-silane 
• 315204-07-0 (E)-4-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-but-2-en-1-ol 
• 315204-09-2 (2R,4S,5R)-2-Phenyl-4-((2R,3R)-3-vinyl-oxiranylmethyl)-[1,3]dioxan-5-ol 
• 315203-96-4 Toluene-4-sulfonic acid (4aR,5aS,6aR,8S,9S,10aS,11aR,13aS)-9-hydroxy-2,2,10a-trimethyl-8-(2-triisopropylsilanyloxy-ethyl)-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ylmethyl ester 
• 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 
• 315204-05-8 Acetic acid (2S,3R,4aR,5aR,8S,9R,10aS,11aR)-9-acetoxymethyl-3-benzyloxy-2-(2-benzyloxy-ethyl)-4a-ethanesulfonyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester 
• 315203-91-9 Acetic acid (2S,3R,4aR,5aR,8S,9R,10aS,11aR)-9-acetoxymethyl-3-benzyloxy-2-(2-benzyloxy-ethyl)-4a-ethylsulfanyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester 
• 315203-83-9 Acetic acid (2S,3R,4aS,5aR,8S,9R,10aS,11aR)-9-acetoxymethyl-3-benzyloxy-2-(2-benzyloxy-ethyl)-4a-methyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester 
• 315203-95-3 (4aR,5aS,6aR,8S,9S,10aS,11aR,13aS)-9-Hydroxymethyl-2,2,10a-trimethyl-8-(2-triisopropylsilanyloxy-ethyl)-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ol 
• 315204-06-9 (4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9-Benzyloxy-8-(2-benzyloxy-ethyl)-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalene 
• 315203-82-8 (4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-2,2,9,10a-Tetramethyl-8-(2-triisopropylsilanyloxy-ethyl)-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ol 
• 315203-94-2 Triisopropyl-[2-((4aR,5aS,6aR,8S,10aS,11aR,13aS)-2,2,10a-trimethyl-9-methylene-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-8-yl)-ethoxy]-silane 
• 315203-92-0 (4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-2,2,10a-Trimethyl-8-(2-triisopropylsilanyloxy-ethyl)-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ol 
• 315203-93-1 (4aR,5aS,6aR,8S,10aS,11aR,13aS)-2,2,10a-Trimethyl-8-(2-triisopropylsilanyloxy-ethyl)-decahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-one 

Downstream Products

• 346584-11-0 (E)-4-((4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9-Benzyloxy-2,2,9,10a-tetramethyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-8-yl)-but-2-enoic acid benzyl ester 

Relevant academic research and scientific papers

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

A synthetic route to the EFGH ring system (3) of gambierol (1), a marine polyether toxin isolated from the dinoflagellate Gambierdiscus toxicus, has been developed. The present synthesis features convergent coupling of the F and H rings followed by ring-closure of the G ring based on the B-alkyl Suzuki reaction of lactone-derived enol phosphates. An angular methyl group at C23 was stereoselectively introduced by treatment of sulfone 32 with trimethylaluminum. Installation of a tertiary alcohol at C21 was accomplished through stereoselcetive dihydroxylation of exo-methylene 36 followed by selective formation of the primary p-toluensulfonate and treatment of the resultant monotosylate 40 with lithium aluminum hydride. Finally, formation of the E ring as a lactone form completed the synthesis of 3.