315204-07-0

Upstream product

• 213815-23-7 (E)-4-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-but-2-enoic acid methyl ester 

Downstream Products

• 315204-08-1 ((2R,3R)-3-(((2R,4S,5R)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1,3-dioxan-4-yl)methyl)oxiran-2-yl)methanol 
• 346584-04-1 {(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7R,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-tetrahydro-pyran-3-yloxy}-tert-butyl-dimethyl-silane 
• 346584-05-2 (2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7R,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-tetrahydro-pyran-3-ol 
• 346584-06-3 (2R,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7R,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-dihydro-pyran-3-one 
• 346584-03-0 (2R,4aR,6S,7R,9aS)-6-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol 
• 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 
• 346584-08-5 (2R,4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9-Benzyloxy-8-(2-benzyloxy-ethyl)-2-phenyl-decahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-10a-ol 
• 382615-99-8 (2S,3R,5S,6R)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-6-(9-bora-bicyclo[3.3.1]non-9-ylmethyl)-5-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran 
• 346584-10-9 2-((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)-ethanol 
• 315204-12-7 tert-Butyl-dimethyl-[(2R,4S,5R)-2-phenyl-4-((2R,3R)-3-vinyl-oxiranylmethyl)-[1,3]dioxan-5-yloxy]-silane 
• 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 

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.