247184-52-7

Upstream product

• 81037-07-2 (2S,5S)-2-(tert-butyl)-5-methyl-1,3-dioxolan-4-one 
• 247184-47-0 (2S,6R,8S)-8-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-ene-2-carbaldehyde 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 247184-60-7 {3-[(4S,5R)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-prop-1-ynyl}-trimethyl-silane 
• 328535-10-0 (2R,4S,5R)-2-(4-Methoxy-phenyl)-5-methyl-4-prop-2-ynyl-[1,3]dioxane 
• 243464-47-3 (2S,10S,11R)-1-(tert-Butyl-diphenyl-silanyloxy)-12-(4-methoxy-benzyloxy)-11-methyl-2,10-bis-trimethylsilanyloxy-dodec-7-yn-6-one 
• 243464-41-7 (E)-(2S,10S,11R)-1-(tert-Butyl-diphenyl-silanyloxy)-12-(4-methoxy-benzyloxy)-8,11-dimethyl-2,10-bis-trimethylsilanyloxy-dodec-7-en-6-one 
• 328534-76-5 (2S,10S,11R)-1-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-12-(4-methoxy-benzyloxy)-11-methyl-10-trimethylsilanyloxy-dodec-7-yn-6-one 
• 247184-51-6 tert-Butyl-{(2S,6R,8S)-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethoxy}-diphenyl-silane 
• 243464-44-0 (2S)-6-benzyloxy-1-(tert-butyldiphenylsilyloxy)-hex-4-yn-2-ol 
• 328535-14-4 {(2S,6R,8S)-8-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl}-methanol 
• 243464-45-1 (S)-6-(tert-butyl-diphenylsilyloxy)-hexane-1,5-diol 
• 203926-59-4 (2R,3S)-1-(4-Methoxy-benzyloxy)-2-methyl-6-trimethylsilanyl-hex-5-yn-3-ol 
• 203926-60-7 (2R,3S)-1-(4-Methoxy-benzyloxy)-2-methyl-hex-5-yn-3-ol 

Relevant academic research and scientific papers

Expedient access to the okadaic acid architecture: A novel synthesis of the C1-C27 domain

A newly designed synthetic entry to the C1-C27 domain of okadaic acid has been developed. This incorporates substantial improvements in the preparations of the key okadaic acid building blocks representing the C3-C8, C9-C14, and C16-C27 portions. The synthesis of the C3-C8 lactone used (R)-glycidol as the origin of the C4 stereogenic center and featured a late-stage optional incorporation of the C7 hydroxyl group. The complementary C9-C14 fragment was synthesized in a concise route from (R)-3-tert-butyldimethylsilyloxy-2-methylpropanal and propargyl bromide. Assembly of the C3-C14 spiroketal-containing intermediate from the constituent fragments revealed a dramatic effect of C7 functionalization upon spiroketalization efficiency. In contrast, both (9E)- and (9Z)-enones converged readily to the C8 spiroketal upon treatment with acid. Modifications to the central C16-C27 fragment of okadaic acid included the early replacement of benzylic protecting groups by more suitable functionalities to facilitate both the generation of the C15-C27 intermediate and the deprotection of the final products. These modular building blocks were deployed for the synthesis of the C1-C27 scaffold of 7-deoxyokadaic acid. This work demonstrates improvements in the formation of versatile okadaic acid intermediates, as well as a reordering of fragment couplings. This alternative order of coupling was designed to promote the late stage incorporation of nonnatural lipophilic extensions from the C27 terminus.

Total synthesis of the marine natural product 7-deoxy-okadaic acid: A potent inhibitor of serine/threonine-specific protein phosphatases

A small change to the structure of okadaic acid (1), the omission of the single hydroxy group at C7, facilitated substantially the first total synthesis of the derivative 7-deoxyokadaic acid (2). The conformation of 2 is in agreement with that of 1 and th