952103-33-2

Upstream product

• 952103-50-3 C₁₈H₂₂NO₄I 
• 69739-34-0 t-butyldimethylsiyl triflate 

Relevant academic research and scientific papers

Total synthesis of the originally proposed and revised structures of palmerolide A

(Chemical Equation Presented) In the palm of your hand: Total syntheses of the originally proposed and revised structures of the marine antitumor agent palmerolide A (see picture, originally proposed structure had opposite configurations at the positions indicated in red) were accomplished through a modular strategy that features a ring-closing metathesis to stereoselectively form the C8=C9 bond and concurrently form the macrocycle.

Total synthesis of the originally proposed and revised structures of palmerolide A and isomers thereof

Palmerolide A is a recently disclosed marine natural product possessing striking biological properties, including potent and selective activity against the melanoma cancer cell line UACC-62. The total syntheses of five palmerolide A stereoisomers, including the originally proposed (1) and the revised [ent-(19-epi-20-epi-1)] structures, have been accomplished. The highly convergent and flexible strategy developed for these syntheses involved the construction of key building blocks 2, 19-epi-2, 20-epi-2, ent-2, 3, ent-3, 4, and enf-4, and their assembly and elaboration to the target compounds. For the union of the building blocks, the Stille coupling reaction, Yamaguchi esterification, Horner-Wadsworth-Emmons olefination, and ring-closing metathesis reaction were employed, the latter being crucial for the stereoselective formation of the macrocycle of the palmerolide structure. The Horner-Wadsworth-Emmons olefination and the Yamaguchi lactonization were also investigated and found successful as a means to construct the palmerolide macrocycle. The syntheses were completed by attachment of the enamide moiety through a copper-catalyzed coupling process.