A synthesis of herboxidiene

The Total Synthesis and Biological Properties of the Cytotoxic Macrolide FD‐891 and Its Non‐Natural (Z)‐C12 Isomer

“…The latter was transformed into methyl ketone 55 by the intermediate acid 53 and the Weinreb [15] amide 54. [40] Reduction of 55 under chelation control [17] to 56 and O-methylation by using methyl triflate and proton sponge [41] stereoselectively afforded 57. Hydrogenolytic O-debenzylation to 58, introduction of the tetrazolylthio [42] moiety via Mitsunobu reaction by using nBu 3 P [43] and Mo(VI)-catalysed sulfide-sulfone oxidation [44] gave rise to the desired aryl sulphone 25.…”

Identification of the Herboxidiene Biosynthetic Gene Cluster in Streptomyces chromofuscus ATCC 49982

“…Additionally, it also has strong cytotoxic activities and induces both G 1 and G 2 /M arrest in human tumor cell line WI-38 (50% inhibitory concentrations range from 3.7 nM to 0.99 M) (9,23). Because of its promising biological activities, several chemical synthetic approaches toward compound 1 have recently been attempted (5,7,8,26). One of the most recent chemical syntheses of compound 1 was accomplished from two lactate-derived chiral ketones in 14 steps with an 8% overall yield (21).…”

Herboxidiene biosynthesis, production, and structural modifications: prospect for hybrids with related polyketide

“…Small molecules that act by affecting the functions of spliceosome are limited in number (Roybal and Jurica 2010). Because of its multiple promising biological activities, various approaches have been used for the biosynthesis and production of a number of herboxidiene derivatives (Blakemore and Kocieński 1999;Edmunds et al 2000;Zhang and Panek 2007;Ghosh and Li 2010;Jha et al 2015).…”