138331-70-1

Basic information

• Product Name: Paspalinine
• CAS NO: 138331-70-1
• Molecular Weight: 433.547
• Mol File: 138331-70-1.mol

Chemical Properties

• CAS DataBase Reference: Paspalinine(CAS DataBase Reference)
• NIST Chemistry Reference: Paspalinine(138331-70-1)
• EPA Substance Registry System: Paspalinine(138331-70-1)

Safety Data

• Hazardous Substances Data: 138331-70-1(Hazardous Substances Data)

Upstream product

• 129896-07-7 (R)-3,3-dimethyl-1,4-dioxaspiro[4.4]nonane-2-carbaldehyde 
• 106268-98-8 (S)-(3,3-dimethyloxiran-2-yl)methyl 4-nitrobenzoate 
• 119816-63-6 <3aR-(3aα,9aα,9bβ)>-3,3a,4,6,8,9,9a,9b-Octahydro-9a,9b-dimethylspiro<7H-benzindene-7,2'-<1,3>dioxolan>-1(2H)-one 
• 138235-30-0 C₁₈H₂₆O₃S 
• 129896-00-0 C₂₁H₂₃NO 
• 138235-32-2 4-Nitro-benzoic acid (S)-3,3-dimethyl-1,4-dioxa-spiro[4.4]non-2-ylmethyl ester 
• 138235-44-6 C₂₃H₂₉N₃ 
• 556-82-1 3-methyl-2-buten-1-ol 
• 148493-54-3 tributyl (o-tert-butyloxycarbonylaminophenyl) stannane 
• 1142931-86-9 paspalinine-13-ene 

Downstream Products

• 144446-23-1 β-aflatrem 
• 70553-75-2 aflatrem 

Relevant articles and documents

Total synthesis of the tremorgenic indole diterpene paspalinine

Succinct and stereoselective: A high-yielding two-step indole ring installation comprising the Stille cross-coupling and a PdII-mediated oxidative heterocyclization was exploited in a concise total synthesis of paspalinine. The trans-anti-trans CDE fused ring system of the heptacyclic natural product was established highly stereoselectively through hydroxy-directed cyclopropanation and allylic selenoxide rearrangement. Copyright

Asymmetric Total Synthesis of Indole Diterpenes Paspalicine, Paspalinine, and Paspalinine-13-ene

Paspaline-derived indole diterpenes (IDTs) are structurally complex mycotoxins with unique tremorgenic activity. Reported are asymmetric total syntheses of three paspaline-derived IDTs paspalicine, paspalinine and paspalinine-13-ene. Our synthesis features a green Achmatowicz rearrangement/bicycloketalization for the efficient construction of FG rings (75 % yield) and a cascade ring-closing metathesis of dienyne for highly regioselective formation of CD rings (72 % yield). Other highlights include four palladium-mediated reactions (Stille, aza-Wacker, Suzuki, and Heck) to forge the BE rings and the installation of two continuous all-carbon quaternary stereocenters via reductive ring-opening of cyclopropane and α-methylation of the conjugate ester. Our new synthetic strategy is expected to be applicable to the chemical synthesis of other paspaline-derived IDTs and will facilitate the bioactivity studies of these agriculturally and pharmacologically important IDTs.

Indole diterpene synthetic studies. 8. The total synthesis of (+)-paspalicine and (+)-paspalinine

The development of a unified synthetic strategy for the indole diterpene tremorgens has led to the first total synthesis of (+)-paspalicine (2) and (+)-paspalinine (3), in 22 and 23 steps, respectively. The cornerstone of the approach is the intermediacy