30315-04-9Relevant articles and documents
An Enantioselective Synthesis of (+)-Picrasin B, (+)-Δ2-Picrasin B, and (+)-Quassin from the R-(-) Enantiomer of the Wieland-Miescher Ketone
Kim, Moonsun,Kawada, Kenji,Gross, Raymond S.,Watt, David S.
, p. 504 - 511 (2007/10/02)
An enantioselective total synthesis of (+)-picrasin B (1), (+)-Δ2-picrasin B (11), and (+)-quassin (12) from the R-(-) enantiomer of the Wieland-Miescher ketone (3) employed an A-AB-ABC-ABCD sequence to assemble the tetracyclic skeleton.The cru
AN ENANTIOSELECTIVE TOTAL SYNTHESIS OF (+)-PICRASIN B1
Kenji, Kawada,Moonsun, Kim,Watt, David S.
, p. 5989 - 5992 (2007/10/02)
An enantioselective total synthesis of (+)-picrasin B (1) from the R-(-)-enantiomer of the Wieland-Miescher ketone (4) employed an A-AB-ABC-ABCD sequence to assemble the tetracyclic skeleton and relied upon a free radical cyclization of an α-bromoacetal to an enone in order to introduce the D ring and a manganese(III) acetate oxidation of a tricyclic enone intermediate in order to introduce the C-11 oxygen substituent.
A PARTIAL SYNTHESIS OF PICRASIN B AND Δ2-PICRASIN B1
Kenji, Kawada,Moonsun, Kim,Watt, David S.
, p. 5985 - 5988 (2007/10/02)
The regioselective reductive demethylation of the O-methyldiosphenol functionality in the A ring of quassin (3) with chlorotrimethylsilane and sodium iodide furnished picrasin B (1).Swern oxidation of 1 furnished Δ2-picrasin B (2), and O-methylation of 2 regenerated quassin (3).