The First Stereoselective Total Synthesis of Putaminoxin E and Its Epimer and Evaluation of Their Biological Properties

Abstract

Putaminoxin E, a natural nonanolide, and its C-9 epimer were synthesized for the first time starting from pentane-1,5-diol and butyraldehyde. The synthetic sequences involve Maruoka asymmetric allylation, Sharpless kinetic resolution,

Rhodium-Catalyzed Regio- and Enantioselective Addition of N-Hydroxyphthalimide to Allenes: A Strategy To Synthesize Chiral Allylic Alcohols

“…Inspired by the above results, the new NHPI allylation was applied to the formal total synthesis of putaminoxin E, which possesses interesting cyctotoxic activity . As shown in Scheme , 1u could be regioselectively and enantioselectively allylated to supply the corresponding product 3ua in 87% yield with 90% ee.…”

“…As shown in Scheme , 1u could be regioselectively and enantioselectively allylated to supply the corresponding product 3ua in 87% yield with 90% ee. Allylic alcohol 5ua , which has been used as an important intermediate in a total synthesis of putaminoxin E, was derived from subsequent deprotection of N -phthalimide in 72% yield and 88% ee …”

“…Inspired by the above results, the new NHPI allylation was applied to the formal total synthesis of putaminoxin E, which possesses interesting cyctotoxic activity. 22 As shown in Scheme 4, 1u could be regioselectively and enantioselectively allylated to supply the corresponding product 3ua in 87% yield with 90% ee. Allylic alcohol 5ua, which has been used as an important intermediate in a total synthesis of putaminoxin E, was derived from subsequent deprotection of N-phthalimide in 72% yield and 88% ee.…”

The first stereoselective total synthesis of a new antitumour and anti-inflammatory neolignan, surinamensinol A

“…For the synthesis of the chiral diol 3, 3,4,5-trimethoxy benzaldehyde (5) was treated with vinyl magnesium bromide to produce the alcohol 7 (Scheme 2). 4 The alcohol 7 was oxidized with IBX and the corresponding ketone was subjected to chiral reduction using (R)-(+) 2-methyl-CBS-oxazaborolodine and BH 3 SMe 2 to furnish the chiral alcohol 8 (ee 91%). 5 The free hydroxyl group of 8 was protected as a Bn-ether (9) by treatment with BnBr and NaH.…”

The First Stereoselective Total Synthesis of Putaminoxin E and Its Epimer and Evaluation of Their Biological Properties

“…The correct wording of the paragraph beneath Table 2 on the third page of the original article [1] is given below. We apologize for any confusion this may have caused.…”