01408nas a2200229 4500008004100000022001400041245007000055210006900125260000800194300001400202520068900216653001300905653001600918653002100934653002600955653002100981653002001002100001901022700002401041700001901065856009401084 2018 eng d a1434-193X00aFirst total synthesis of the proposed structure of pandangolide 10 aFirst total synthesis of the proposed structure of pandangolide cJUL a3352-33643 a
The first total synthesis of the proposed structure of pandangolide 1 is reported. The synthesis was carried out using both an organocatalytic approach and a chiral-pool approach. The required stereochemistry at C-3 and C-5 was installed by using an organocatalytic aldol reaction and a stereoselective ketone reduction. The construction of the 12-membered core was achieved by 2-methyl-6-nitrobenzoic anhydride-mediated Shiina lactonization. The structure of target molecule was confirmed unambiguously by single-crystal X-ray analysis, but the optical rotation and NMR spectroscopic data of the synthetic pandangolide 1 were found to be inconsistent with the natural product.
10alactones10aMacrocycles10aNatural products10astructure elucidation10asynthesis design10aTotal synthesis1 aShow, Krishanu1 aGonnade, Rajesh, G.1 aKumar, Pradeep uhttp://library.ncl.res.in/content/first-total-synthesis-proposed-structure-pandangolide-1