1402820-10-3

Basic information

• Product Name: C₁₂H₁₂O₂
• Synonyms: C₁₂H₁₂O₂
• CAS NO: 1402820-10-3
• Molecular Weight: 188.226
• Mol File: 1402820-10-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: C₁₂H₁₂O₂(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₂H₁₂O₂(1402820-10-3)
• EPA Substance Registry System: C₁₂H₁₂O₂(1402820-10-3)

Safety Data

• Hazardous Substances Data: 1402820-10-3(Hazardous Substances Data)

Upstream product

• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 102794-92-3 (2R,4R)-4-formyl-2-phenyl-1,3-dioxane 
• 3969-69-5 (-)-cis-4-hydroxymethyl-2-phenyl-1,3-dioxolane 

Downstream Products

• 1447052-01-8 C₂₉H₄₈O₇SSi 

Relevant articles and documents

Total Synthesis and Biological Evaluation of Siladenoserinol A and its Analogues

The total synthesis of siladenoserinol A, an inhibitor of the p53–Hdm2 interaction, has been achieved. AuCl3-catalyzed hydroalkoxylation of an alkynoate derivative smoothly and regioselectively proceeded to afford a bicycloketal in excellent yield. A glycerophosphocholine moiety was successfully introduced through the Horner–Wadsworth–Emmons reaction using an originally developed phosphonoacetate derivative. Finally, removal of the acid-labile protecting groups, followed by regioselective sulfamate formation of the serinol moiety afforded the desired siladenoserinol A, and benzoyl and desulfamated analogues were also successfully synthesized. Biological evaluation showed that the sulfamate is essential for biological activity, and modification of the acyl group on the bicycloketal can improve the inhibitory activity against the p53–Hdm2 interaction.

Exploiting hidden symmetry in natural products: Total syntheses of amphidinolides C and F

The total synthesis of amphidinolide C and a second-generation synthesis of amphidinolide F have been accomplished through the use of a common intermediate to access both the C1-C8 and the C18-C 25 sections. The development of a Ag-catalyzed cyclization of a propargyl benzoate diol is described to access both trans-tetrahydrofuran rings. The evolution of a Felkin-controlled, 2-lithio-1,3-dienyl addition strategy to incorporate C9-C11 diene as well as C8 stereocenter is detailed. Key controlling aspects in the sulfone alkylation/oxidative desulfurization to join the major subunits, including the exploration of the optimum masking group for the C18 carbonyl motif, are discussed. A Trost asymmetric alkynylation and a stereoselective cuprate addition to an alkynoate have been developed for the rapid construction of the C26-C34 subunit. A Tamura/Vedejs olefination to introduce the C26 side arm of amphidnolides C and F is employed. The late-stage incorporation of the C15, C18 diketone motif proved critical to the successful competition of the total syntheses.