Synthesis and confirmation of the absolute stereochemistry of the (-)-aflastatin A C9-C27 degradation polyol.

Absolute configuration of a polyol fragment of blasticidin A, a specific inhibitor of aflatoxin production.

Blasticidin A (1) and aflastatin A (2), Streptomyces metabolites with similar structures, are specific inhibitors of aflatoxin production by Aspergillus parasiticus. The stereochemistry of the polyol fragment of 1 (3a) containing ten chiral centers was elucidated by applying acetonide and MTPA methods to a variety of acetonide derivatives of 3a, which determined the absolute configuration of 3a...

A highly convergent synthesis of the C1–C31 polyol domain of amphidinol 3 featuring a TST-RCM reaction: confirmation of the revised relative stereochemistry† †Electronic supplementary information (ESI) available: Experimental details, spectral data, correlation with the natural product and copies of spectra. See DOI: 10.1039/c5sc00814j Click here for additional data file.

Complex aldol reactions for the construction of dense polyol stereoarrays: synthesis of the C33-C36 region of aflastatin A.

[reaction: see text]. Facial selectivity in the addition of boron enolates of alpha-oxygenated ketones to anti-disposed alpha,beta-bisalkoxy aldehydes is controlled by the aldehyde vicinal diol protecting group. Protection of the diol as an acetonide results in the exclusive formation of the anti-syn-anti stereoarray found in the C(33)-C(36) region of aflastatin A.

A highly convergent synthesis of the C1-C31 polyol domain of amphidinol 3 featuring a TST-RCM reaction: confirmation of the revised relative stereochemistry.

The concise enantioselective synthesis of the revised C1-C31 fragment of the polyketide amphidinol 3 was accomplished in 16 steps and 12.8% overall yield. Salient features of the strategy include chemoselective Weinreb amide coupling and concomitant CBS reduction for the preparation of the C1-C15 tris-syn-1,5-diol motif and a temporary silicon-tethered ring-closing metathesis (TST-RCM) reaction...

SYNTHESIS OF HIGH ASPECT RATIO SILVER NANOWIRES: PARAMETRIC STUDY OF THE POLYOL PROCESS

Silver nanowires (AgNWs) are considered as one-dimensional nanostructures, which have received much attention due to their nanoscale size, high aspect ratio, high electrical and thermal conductivity, optical transparency and high mechanical stability. Preparation of AgNWs by polyol process is remarkably sensitive to the interactions between synthesis parameters. In this study, the effect of the...