73787-23-2Relevant 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
TOTAL SYNTHESIS OF (+)-PEDERIN. 1. STEREOCONTROLLED SYNTHESIS OF (+)-BENZOYLPEDAMIDE
Nakata, Tadashi,Nagao, Shigeto,Mori, Nobuyuki,Oishi,Takeshi
, p. 6461 - 6464 (2007/10/02)
(+)-Benzoylpedamide (5), a right half of (+)-pederin (1), was synthesized stereoselectively based on the newly developed method for the synthesis of 1,3-syn- and 1,3-anti-polyols.
REMOTE ACYCLIC STEREOCONTROL; CHIRAL SYNTHESIS OF (+)-PEDAMIDE
Matsumoto, Takeshi,Matsuda, Fuyuhiko,Hasegawa, Kazuo,Yanagiya, Mitsutoshi
, p. 2337 - 2344 (2007/10/02)
Synthesis of optically active pedamide (3), one of the tetrahydropyran moieties of the potent insect poison pederine (1), has been accomplished through a new, remote controlled asymmetric reduction of a ketone as key step.
Synthetic Approaches to Pederin. A Synthesis of (+/-)-Benzoylpedamide
Kocienski, Philip,Willson, Timothy M.
, p. 1011 - 1012 (2007/10/02)
A Lewis acid-catalysed addition of Me3SiCN to a 4-oxo-3,4-dihydro-2H-pyran is a key step in the synthesis of (+/-)-benzoylpedamide (2).
TOTAL SYNTHESIS OF (+)-PEDAMIDE. A NEW, REMOTE CONTROLLED ASYMMETRIC INDUCTION
Yanagiya, Mitsutoshi,Matsuda, Fuyuhiko,Hasegawa, Kazuo,Matsumoto, Takeshi
, p. 4039 - 4042 (2007/10/02)
Total synthesis of optically active pedamide 2, one of the tetrahydropyran moieties of the potent insect poison pederine 1, was achieved by employing a new, remote controlled asymmetric reduction of a ketone as key step.
