Synthesis of tetracyclic indolin-3-ones through Pd-catalyzed intramolecular deacetylative dearomatization of 3-acetoxy-indoles.

An efficient palladium-catalyzed intramolecular deacetylative dearomatization reaction of 3-acetoxyindoles has been developed. A range of tetracyclic indolin-3-ones bearing C2-quaternary stereocenters are achieved in good yields, showing a wide substrate scope for this reaction. A preliminary enantioselective reaction is established to furnish the product in 63% ee by using (R,R,R)-phosphoramide-PE as a chiral ligand.

X-ray structure of 1,3,4-tri-O-acetyl-2-deoxy-beta-d-erythro-pentopyranose.

Peracetylated 2-deoxy-d-erythro-pentose (2-deoxy-d-ribose) was synthesized through the acetylation of 2-deoxy-d-ribose with acetic anhydride in pyridine, and the products (including all four ring forms) exist in form of either a white solid or a syrup. A single crystal of 1,3,4-tri-O-acetyl-2-deoxy-beta-d-erythro-pentopyranose was obtained from the syrup and its structure was determined by X-ray diffraction. The crystal adopts the (1)C(4) conformation, presenting an orthorhombic system, space group P2(1)2(1)2(1) with Z=4, unit cell dimensions a=7.2274 (3)A, b=8.0938 (5)A, and c=22.0517 (11)A.