82508-32-5

Usage

Uses

Pseudolaric Acid A is a cytotoxic natural product and a potential antitumor drug.

InChI:InChI=1/C22H28O6/c1-14-7-11-21-12-9-17(22(21,13-8-14)27-16(3)23)20(4,28-19(21)26)10-5-6-15(2)18(24)25/h5-7,10,17H,8-9,11-13H2,1-4H3,(H,24,25)/b10-5+,15-6+/t17?,20?,21?,22-/m0/s1

Upstream product

• 75-36-5 acetyl chloride 
• 82508-37-0 deacetylpseudolaric acid A 
• 915708-21-3 1-(2,2-diethyl-4-methyl-[1,3]dioxolan-4-yl)-8a-hydroxy-6-methyl-2,3,4,7,8,8a-hexahydro-1H-azulene-3a-carbaldehyde 
• 915708-16-6 3-(2,2-diethyl-4-methyl-[1,3]dioxolan-4-yl)-8a-hydroxymethyl-6-methyl-2,3,4,5,8,8a-hexahydro-1H-azulen-3a-ol 
• 915708-15-5 3-(2,2-diethyl-4-methyl-[1,3]dioxolan-4-yl)-8a-(4-methoxy-benzyloxymethyl)-6-methyl-2,3,4,5,8,8a-hexahydro-1H-azulen-3a-ol 
• 915708-14-4 8-chloro-2-(2,2-diethyl-4-methyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxymethyl)-8-methyl-11-oxa-tricyclo[5.3.1.0^1,5]undecane 
• 915708-12-2 2-(2,2-diethyl-4-methyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxymethyl)-11-oxa-tricyclo[5.3.1.0^1,5]undecan-8-one 
• 915708-13-3 2-(2,2-diethyl-4-methyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxymethyl)-8-methyl-11-oxa-tricyclo[5.3.1.0^1,5]undecan-8-ol 
• 111086-19-2 methyl 2-(2-propenyl)-3-oxo-6-methylhept-6-enoate 
• 3897-04-9 methyl 2-acetylpent-4-enoate 
• 108-24-7 acetic anhydride 

Downstream Products

• 82508-37-0 deacetylpseudolaric acid A 

Relevant academic research and scientific papers

A concise approach for the total synthesis of pseudolaric acid A

A new strategy for the stereoselective total synthesis of natural product pseudolaric acid A (1) was accomplished in 16 steps from commercially available starting material, featuring a samarium diiodide (SmI2)-mediated intramolecular alkene-ketyl radical cyclization and a ring-closing metathesis (RCM) reaction to stereoselectively cast the unusual trans-fused [5-7]-bicyclic core of pseudolaric acid A (1).

Total synthesis of pseudolaric acid A

(Chemical Equation Presented) The antiangiogenic and cytotoxic natural product pseudolaric acid A ((-)-1) has been obtained by a 26-step synthetic route. This enantioselective synthesis employed an intramolecular carbene cyclization cycloaddition cascade