Stereoselective synthesis of (−)-protulactone A

New Synthetic Approach to Protulactone A and Structural Analogues

“…3 The Liu group achieved a synthesis of (–)-protulactone A starting from d -mannose. 4 As a part of our ongoing studies on the synthesis of natural products containing furofuranone motifs, 5 6 we recently published details of our total synthesis of PLA , along with its X-ray crystal structure analysis and biological evaluation. 7 Here, we describe a new synthetic approach to the natural product PLA and several of its analogues, starting from d -galactose, and we report a preliminary study of the antiproliferative activities of the products, together with a structure–activity­ relationship (SAR) analysis.…”

Stereoselective Total Synthesis of (+)-Brevipolide H from d-Galactal

“…HRMS were acquired using a Q-TOF analyzer in MeOH as solvent. 1 H and 13 C NMR were recorded on 400 MHz and 100 Hz spectrometers. Chemicals shifts () were expressed in ppm relative to residual CDCl 3 or MeOD.…”

“…Considering the impressive broad-band biological activities of brevipolides and their potential medicinal application, we sought to develop an enantioselective synthesis of brevipolides. As part of our ongoing research program on the total synthesis of biologically active natural products using carbohydrate as chiral pool, [10][11][12][13] herein, we describe a concise and stereoselective synthesis of natural (+)-brevipolide H (8) from D-galactal and ethyl Llactate.…”

Bioinspired synthesis and biological evaluation of ent-protulactones A and B

“…To date, four syntheses of protulactone A have been disclosed, including ours. 4–7 Pioneering synthetic studies of these natural bicyclic lactones were conducted by the Gracza group. 4 In 2017, Gracza and co-workers reported the first total synthesis and configuration assignment of naturally occurring (+)-protulactone A ( 1 ) and its diastereomers, along with their effects on the antiproliferative activity of the NCI60 cancer cell line panel.…”

“…As part of our interest in the total synthesis of biologically active natural products based on the chiral pool, we have recently accomplished the total synthesis of unnatural enantiomer (−)-protulactone A ( 1′ ) from d -mannose in nine steps and 14.7% overall yields using a cascade reaction of acetonide deprotection/lactonization/intramolecular oxa-Michael addition/acetal formation as the key step. 5 Very recently, Francuz et al 6 communicated their synthesis of (+)-protulactone A ( 1 ) starting from d -galactose in seven steps with an overall yield of 4.92%. Soon after, the same group disclosed an alternative synthetic approach to synthesize (+)-protulactone A and its derivatives and evaluated their antiproliferative activity against several tumor cell lines.…”