85279-96-5Relevant academic research and scientific papers
Total synthesis of pederin, a potent insect toxin: The efficient synthesis of the right half, (+)-benzoylpedamide
Takemura, Takahiro,Nishii, Yoshinori,Takahashi, Shunya,Kobayashi, Jun'ichi,Nakata, Tadashi
, p. 6359 - 6365 (2007/10/03)
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
Willson, Timothy M.,Kocienski, Philip,Jarowicki, Krzysztof,Isaac, Kim,Hitchcock, Peter M.,Faller, Andrew,Campbell, Simon F.
, p. 1767 - 1782 (2007/10/02)
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
Matsuda, Fuyuhiko,Tomiyoshi, Nobuya,Yanagiya, Mitsutoshi,Matsumoto, Takeshi
, p. 7063 - 7080 (2007/10/02)
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
Willson, Timothy,Kocienski, Philip,Faller, Andrew,Campbell, Simon
, p. 106 - 108 (2007/10/02)
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).
TOTAL SYNTHESIS OF (+)-PEDERINE. A SIMPLE SYNTHETIC METHOD FOR N-(1-METHOXYALKYL)AMIDES
Matsuda, Fuyuhiko,Yanagiya, Mitsutoshi,Matsumoto, Takeshi
, p. 4043 - 4046 (2007/10/02)
A mild one-pot method for the synthesis of acyclic N-(1-methoxyalkyl)amides starting from carboxylic acids and methyl imidates had been developed and applied to the total synthesis of the insect poison pederine 1.
