203454-75-5

Upstream product

• 203454-71-1 [2R]-1-triphenylmethoxy-2-hydroxy-4-pentene 
• 65291-30-7 (R)-(+)-trityl glycidyl ether 
• 100-52-7 benzaldehyde 
• 203454-73-3 [2E,5R]-5-hydroxy-6-(triphenylmethyloxy)-N-methyl-N-methoxy-2-hexenamide 

Downstream Products

• 203454-81-3 (1S)-1-(2-naphthyl)ethyl (3S,5S)-3-tert-butyldimethylsilyloxy-5-methoxy-8-[2-phenyl-4(R)-(triphenylmethyloxy)-methyl-1,3-dioxan-6-(S)-yl]-octan-7-on-1-oate 
• 203516-58-9 C₇₆H₁₂₆O₁₂Si₄ 
• 203516-59-0 C₇₁H₁₀₆O₁₆Si₂ 
• 246510-20-3 C₆₇H₁₀₂O₁₄Si₂ 
• 203516-68-1 C₆₄H₉₈O₁₂Si₂ 
• 203454-79-9 (3S,5S)-3-tert-butyldimethylsilyloxy-5-hydroxy-8-[2-phenyl-4-(R)-(triphenylmethyloxy)methyl-1,3-dioxan-6(S)-yl]-octan-7-on-1-oic acid-2(S)-napthylethanol ester 
• 187819-45-0 [2R,4S,6S]-4-(propan-2-one)-6-[(2-triphenylmethyloxy)-ethyl]-2-phenyl-1,3-dioxane 

Relevant academic research and scientific papers

Enantioselective total synthesis of altohyrtin C (spongistatin 2)

The first total synthesis of a spongipyran macrolide, altohytrin C, is described. The convergent synthesis strategy relies on a regioselective macrolactonization, a stereoselective Wittig coupling of the two major synthetic fragments, a complex anti aldol reaction to join the C1-C15 and C16-C28 spiroketal regions, and an anomeric sulfone acylation to join the C29-C37 and C38-C43 pyran regions. The incorporation of the C44- C51 sidechain in the final stages of the synthesis establishes a viable route for the construction of variants in this pharmacologically important region. Methodological developments en route to the total synthesis include a 1,5 antiselective methyl ketone aldol reaction and a diastereoselective approach to Lewis acid mediated β-C-glycosidation. Completion of the synthesis has confirmed the stereochemical assignments proposed in the altohyrtin series and has established the identity of the altohyrtin and spongistatin marine macrolides.

Enantioselective Synthesis of Altohyrtin C (Spongistatin 2): Synthesis of the AB- and CD-Spiroketal Subunits

Keywords: altohyrtin; antitumor agents; natural products; spongistatin; total synthesis