120093-52-9

Upstream product

• 120093-50-7 (R)-(-)-3,7-dimethyl-2-methylene-6-octen-1-ol 
• 71504-25-1 (R)-2-Dimethylaminomethyl-3,7-dimethyl-oct-6-enal 
• 120093-49-4 (3R)-α-methylene-3,7-dimethyl-6-octen-1-al 
• 18951-85-4 (R)-citronellic acid 
• 2385-77-5 (R)-Citronellal 
• 120093-51-8 [2-((R)-1,5-Dimethyl-hex-4-enyl)-oxiranyl]-methanol 
• 99-33-2 3,5-dinitrobenoyl chloride 

Downstream Products

• 120093-56-3 (2R,3R)-2,3,7-Trimethyl-2-<(3,5-dinitrobenzoyl)oxy>-6-octenyl 3,5-Dinitrobenzoate 

Relevant academic research and scientific papers

Stereoselective Synthesis of the Pyrrolizidine Alkaloids (-)-Integerrimine and (+)-Usaramine

Two routes to the pyrrolizidine alkaloid (-)-integerrimine (1) are described.The first, starting from methyl (R)-(-)-3-hydroxy-2-methylpropionate, proceeded in 19 steps to integerrinecic acid lactone (5) which was transformed to the necic acid derivative 30.The latter was coupled to protected retronecine 31, and the synthesis of 1 was completed by lactonization employing Vedejs' protocol.A second, shorter synthesis of (-)-1 was accomplished via 5, starting from (R)-(+)-β-citronellol (36).This pathway invoked Katsuki-Sharpless epoxidation of 42 for stereoselective construction of the tertiary alcohol of integerrinecic acid.A parallel sequence proceeding via the stereoisomeric epoxide 44 led to the necic acid segment 75 of the alkaloid (+)-usaramine (2).This acid was coupled to the retronecine borane 82 and then lactonized to 2.

A NOVEL SYNTHESIS OF (+)-INTEGERRINECIC ACID LACTONE FROM R-(+)-β-CITRONELLOL

A new route to (+)-integerrinecic acid, the necic acid component of the macrolactone pyrrolizidine alkaloid integerrimine, has been devised starting from the R enantiomer of β-citronellol and proceeding via γ-lactone, 17.