454474-75-0Relevant 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. 2. A novel approach to a γ-hydroxy butenolide derivative and completion of total synthesis
Takahashi, Shunya,Nakata, Tadashi
, p. 727 - 730 (2007/10/03)
Total synthesis of mucocin (1) was accomplished through a palladium- catalyzed cross coupling reaction of the C10-C34 fragment of I and a newly designed γ-hydroxy butenolide subunit, which was synthesized by taking advantage of radic
