Synthesis of (+)-Muconin via Diastereoselective Oxypalladation

Abstract

Synthesis of (+)-muconin isolated from Rollinia mucosa (Annonaceae) was achieved. Stereoselective construction of a tetrahydrofuran-terahydropyran (THF-THP) ring moiety was performed using diastereoselective oxypalladation in the presence of CuCl2. The cross-coupling reaction of the THF-THP moiety with the γ-lactone portion followed by reduction of the enyne and removal of the protecting groups afforded (+)-muconin.

Stereoselective Total Synthesis of Pyranicin and 4‐Epi‐Pyranicin from Carbohydrate Precursors

“…A gram scale preparation of butenolide fragments 3 a and 3 b in a total of 14 steps from diacetyl L‐rhamnal was also achieved. We believe that this protocol could be a valuable addition to the total synthesis of related annonaceous acetogenins such as mucocin, [25] muconin, [26] and jimenezin, [27] etc . Further, the synthesis of pyranicin C‐15 epimer and biological evaluation of 4‐ epi ‐pyranicin 1 b and application of our protocols for the synthesis of other annonaceous acetogenins and related natural products are currently in progress.…”

Sharpless Asymmetric Dihydroxylation: An Impressive Gadget for the Synthesis of Natural Products: A Review

“…Muconin plays a vital role in combating the uncontrolled cell division in human pancreatic and breast cells [ 129 ]. Considering the wide biological applications of muconin, Sugimoto et al [ 130 ] in 2021 described its total synthesis by applying a number of reaction steps. Acrolein 319 was treated with lauryalmagnesium bromide 320 , thereby providing 321 in 92% yield.…”