130697-10-8Relevant academic research and scientific papers
REMOTE ACYCLIC STEREOCONTROL; CHIRAL SYNTHESIS OF (+)-PEDAMIDE
Matsumoto, Takeshi,Matsuda, Fuyuhiko,Hasegawa, Kazuo,Yanagiya, Mitsutoshi
, p. 2337 - 2344 (1984)
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.
A FORMAL SYNTHESIS OF APLASMOMYCIN. ASSEMBLY OF THE C3-C17 SEGMENT BASED ON 1,3- AND 1,5- ASYMMETRIC REDUCTIONS
Matsuda, Fuyuhiko,Tomiyoshi, Nobuya,Yanagiya, Mitsutoshi,Matsumoto, Takeshi
, p. 3469 - 3488 (2007/10/02)
The C3 - C17 segment of a boron containing ionophoric antibiotic aplasmomycin (1), the key intermediate in Corey's total synthesis of 1, was stereoselectively synthesized in an optically active form.This synthesis involved stereoselective construction of the two segments, (+)-dithiane 3 (C3-C11) and (+)-aldehyde 4 (C12-C17), based on remote controlled asymmetric reductions of the corresponding ketones as key steps and connection of 3 and 4 through the trans-double bond to elaborate the (+)-dithiane 2 (C3-C17), the key intermediate in Corey's total synthesis of 1.
