220772-75-8Relevant academic research and scientific papers
Total synthesis of an antitumor agent, mucocin, based on the "chiron approach"
Takahashi, Shunya,Nakata, Tadashi
, p. 5739 - 5752 (2007/10/03)
The total synthesis of a powerful antitumor acetogenin, mucocin (1), was achieved through a palladium-catalyzed cross-coupling reaction of the THP-THF fragment 2 and a terminal butenolide 3. The key process for construction of the fragment 2 was chelation-controlled addition of ethynylmagnesium chloride to disilyl aldehyde 23a and condensation of the alkyllithium prepared therefrom with THP aldehyde 4 in the presence of CeCl3. Synthesis of the lactone 3 relied on a novel approach by taking advantage of a radical cyclization of acyclic selenocarbonate 6. The three building blocks 4, 5a, and 6 were prepared stereoselectivly from D-galactose (7), 2,5-anhydro-D-mannitol (8), and L-rhamnose (9), respectively. A new and efficient method for desymmetrization of the C2-symmetrical compound 8 is also described.
Total synthesis of an anticancer agent, mucocin. 1. Stereoselective synthesis of the left-half segment
Takahashi, Shunya,Nakata, Tadashi
, p. 723 - 726 (2007/10/03)
The left-half segment of mucocin (1) was stereoselectively synthesized through a coupling reaction of a tetrahydropyranyl aldehyde and a tetrahydrofuran derivative having an ethynyl group, which were prepared from 2,3,4,6-tetra-O-benzyl-D-galactono-1,5-la
