Total synthesis and structure validation of (+)-bistramide C.

Synthesis of derivatives of potent antitumor bistramides D and A leading to the first crystal structure of natural bistramide D.

We report a crystalline derivative of bistramide D synthesized from natural bistramide A, and its structure was determined by X-ray analysis.

Total synthesis of a stereoisomer of bistramide C and assignment of configuration of the natural product.

After the isolation of the bioactive polyether bistramide C from the marine ascidian Lissoclinum bistratum in 1988, NMR spectroscopic investigations over the next 12 years reduced the total number of possible stereoisomers of this compound from 1024 to 32. Based on the preparation of segments of the natural product as well as the total synthesis of a randomly selected stereoisomer of bistramide...

Enantioselective total synthesis of bistramide A.

The enantioselective synthesis of bistramide A has been achieved with a longest linear sequence of 18 steps. The synthetic strategy involves the use of a distereoselective glycolate alkylation, an aldol addition of a chlorotitanium enolate of N-acylthiazolidinthione, and a Sharpless asymmetric epoxidation to synthesize the three key fragments.

Design, synthesis, and biological evaluation of simplified side chain hybrids of the potent actin binding polyketides rhizopodin and bistramide.

The natural products rhizopodin and bistramide belong to an elite class of highly potent actin binding agents. They show powerful antiproliferative activities against a range of tumor cell lines, with IC50 values in the low-nanomolar range. At the molecular level they disrupt the actin cytoskeleton by binding specifically to a few critical sites of G-actin, resulting in actin filament stabiliza...

SYNTHESIS AND STRUCTURE ELUCIDATION OF 1,2,4-TRIAZINO [4,3-b] 1,2,4-TRIAZINES, 1,2,4-TRIAZINO [3,4-C] 1,2,4-TRIAZINES AND 1,2,4-TRIAZINO [4,3-dl l,2,4-TRIAZINES