123483-10-3

Upstream product

• 87045-91-8 C₄₅H₅₉NO₁₁Se 
• 104432-04-4 Benzoic acid (S)-chlorocarbonyl-((2R,4S,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester 
• 87045-91-8 (αS,2R,4R,5R,6R)-N-<(S)-<(2S,4R,6R)-4-(benzoyloxy)-6-<(S)-2,3-dimethoxypropyl>-tetrahydro-5,5-dimethyl-2H-pyran-2-yl>methoxymethyl>-α-(benzoyloxy)tetrahydro-2-methoxy-5,6-dimethyl-4-<(phenylseleno)methyl>-2H-pyran-2-acetamide 
• 27973-72-4 (+)-pederine 
• 98-88-4 benzoyl chloride 
• 85708-35-6 (2S,4R,6R)-4-Benzoyloxy-6-((S)-2,3-dimethoxy-propyl)-5,5-dimethyl-tetrahydro-pyran-2-carboxylic acid 
• 175085-04-8 (S)-2-methoxy-1-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-oxoethyl benzoate 
• 175085-05-9 (S)-2-(benzoyloxy)-2-((2R,5R,6R)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-yl)acetic acid 
• 956117-45-6 (S)-2-chloro-1-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-oxoethyl benzoate 
• 85279-96-5 methyl benzoylpedimidate 
• 73787-23-2 (+)-benzoylpedamide 
• 104432-03-3 (+/-)-benzoylselenopederic acid 

Downstream Products

• 27973-72-4 (+/-)-pederin 
• 27973-72-4 (+)-pederine 

Relevant academic research and scientific papers

Total synthesis of pederin, a potent insect toxin: The efficient synthesis of the right half, (+)-benzoylpedamide

A simple and efficient synthesis of (+)-benzoylpedamide, the right half of pederin, was achieved in 16 steps with a 35% overall yield from (S)-malic acid. The key steps include the SmI2-mediated intramolecular Reformatsky reaction, stereoselective allylation, the Sharpless asymmetric dihydroxylation, and amidation. The total synthesis of pederin was accomplished via coupling of the left and right halves.

Studies related to the synthesis of pederin. Part 2. Synthesis of pederol dibenzoate and benzoylpedamide

Syntheses of the ring B fragments (+)-pederol dibenzoate (2) and (±)-benzoylpedamide (3) of the insect toxin pederin (1) are described. An intramolecular directed aldol condensation was used to construct the tetrahydropyran ring in (+)-pederol dibenzoate

STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-PEDERINE

A mild one-pot method for the synthesis of acyclic N-(1-methoxyalkyl)amides starting from carboxylic acid and methyl imidates has been developed and applied to the first total synthesis of (+)-pederine (1), a potent insect poison.Furthermore, the stereocontrolled total synthesis of 1 was also achieved by employing acid catalyzed double alkoxy-exchange reaction of N-(1-methoxyalkyl)amide group as key step.

The Total Synthesis of (+/-)-Pederin

The conjugate addition of phenylselenomethyl-lithium to the α,β-unsaturated lactone (4) was a key step in a short synthesis of (+/-)-benzoylselenopederic acid (2); union of (2) and (+/-)-benzoylpedamide (3) by a modification of known procedures gave (+/-)-pederin (1).