115352-19-7

Upstream product

• 108-24-7 acetic anhydride 
• 104307-09-7 C₄₁H₅₄O₈ 
• 102795-14-2 (2S,6R,8S,11R)-2-((S)-2-Benzenesulfonyl-1-methyl-ethyl)-11-benzyloxy-4-methyl-8-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-ylmethyl)-1,7-dioxa-spiro[5.5]undec-4-ene 
• 115352-18-6 C₇₄H₉₈O₁₅S 
• 95791-14-3 3-((4aR,6R,7R,8S,8aR)-7-Benzyloxy-8-methoxymethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-propionaldehyde 
• 104307-00-8 C₅₇H₆₄O₈Si 
• 104306-97-0 (R)-1-((4aR,6R,7R,8S,8aR)-7-Benzyloxy-8-methoxymethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-7-(tert-butyl-diphenyl-silanyloxy)-6-(1-ethoxy-ethoxy)-heptan-3-one 
• 115369-32-9 (R)-1-((2R,3R,4R,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-methoxymethoxy-tetrahydro-pyran-2-yl)-7-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-heptan-3-one 
• 109413-94-7 C₃₈H₅₀O₈Si 
• 104306-99-2 C₃₁H₄₄O₈Si 
• 115352-13-1 C₅₇H₇₄O₁₂SSi 
• 115352-14-2 C₅₆H₈₀O₁₁Si 
• 115352-16-4 C₄₉H₇₂O₁₁Si 
• 115352-17-5 C₅₀H₇₄O₁₀Si 

Downstream Products

• 104307-11-1 C₆₈H₉₂O₁₂ 
• 115352-20-0 C₆₅H₈₈O₁₂ 
• 104307-13-3 tribenzyl okadaic acid 
• 104307-12-2 C₆₅H₈₆O₁₂ 
• 78111-17-8 okadaic acid 

Relevant academic research and scientific papers

SYNTHESIS OF A MARINE POLYETHER TOXIN, OKADAIC ACID (4).TOTAL SYNTHESIS.

Three segments A, B and C for okadaic acid synthesis were coupled with each other in order of A+(B+C), the key steps of the twice couplings being between sulfone carbanions and aldehydes.After the B+C coupling , the asymmetric center C-27 was generated by a hydride reduction of the corresponding ketone 16 under electronic control.The second coupling was followed to form the C-14/15 double bond.Oxidation of the α-oxy aldehyde 36 into the carboxylic acid group was achieved with sodium chlorite without C-1/C-2 bond cleavage.The total synthesis of okadaic acid was accomplished in 106 steps from commercially available D-glucose derivative s and butyne-diol.

SYNTHETIC STUDIES TOWARD MARINE TOXIC POLYETHERS THE TOTAL SYNTHESIS OF OKADAIC ACID

The total synthesis of okadaic acid has been accomplished through the coupling of all the segments, A, B and C, by means of sulfone-carbanion strategy.