104307-08-6

Upstream product

• 104307-09-7 C₄₁H₅₄O₈ 
• 104307-07-5 C₅₇H₇₄O₈Si 
• 100-39-0 benzyl bromide 
• 93635-20-2 (2S,3R,6S)-2-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-3-methyl-1,7-dioxa-spiro[5.5]undecane 
• 115352-14-2 C₅₆H₈₀O₁₁Si 
• 115352-13-1 C₅₇H₇₄O₁₂SSi 
• 1250256-05-3 C₄₉H₆₄O₉ 
• 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 
• 115352-16-4 C₄₉H₇₂O₁₁Si 

Downstream Products

• 104307-09-7 C₄₁H₅₄O₈ 
• 115352-19-7 C₇₆H₁₀₀O₁₆S 
• 78111-17-8 okadaic acid 
• 104307-12-2 C₆₅H₈₆O₁₂ 
• 104307-13-3 tribenzyl okadaic acid 
• 104307-11-1 C₆₈H₉₂O₁₂ 
• 115352-20-0 C₆₅H₈₈O₁₂ 
• 115352-18-6 C₇₄H₉₈O₁₅S 

Relevant academic research and scientific papers

Formal total synthesis of okadaic acid via regiocontrolled gold(I)-catalyzed spiroketalizations

Both C19 and C34 spiroketal domains of okadaic acid were assembled using gold(I) chloride catalyzed spiroketalizations, and the two resulting fragments were coupled to give the C15 - C38 fragment of okadaic acid, a known intermediate for the total synthesis of this important natural product.

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.