ChemInform Abstract: One‐Pot Desymmetrization of meso‐1,2‐Hydrocarbon Diols Through Acylation and Oxidation.

Mueller, Christian; Zell, Daniela; Schreiner, Peter R.

doi:10.1002/chin.201005024

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“…A similar cyclodehydration converting erythritol to a tetrahydrofuran was described and granted a similar stereochemistry (Pavlik et al, 2009). The quick transesterification between the two enantiomers in the latter stage was reported (Muller et al, 2009). The putative transformation from 6 to 5 is presented in Scheme 1.…”

Section: Resultsmentioning

confidence: 74%

New erythritol derivatives from the fertile form of Roccella montagnei

Duong¹,

Huynh²,

Chavasiri

et al. 2017

Phytochemistry

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Chemical investigation of the methanol extract of the fertile form of Roccella montagnei collected in Vietnam afforded twelve secondary metabolites, including five new montagnetol derivatives, orsellinylmontagnetols A-D and a furanyl derivative together with seven known compounds. Their chemical structures were elucidated by analysis of 1D and 2D NMR and high resolution mass spectroscopic data. The relative stereochemistry of two chiral centers (C-2 and C-3) of orsellinylmontagnetols A and B was elucidated by comparison of their coupling constants and the specific rotation with those reported in the literature while the absolute stereochemistry was determined by the application of a modified Mosher method for the hydroxy group at C-3. The absolute configuration (2R,3S) of the butanetetraol moiety of these compounds is in accordance with that of erythrin, a recognized chemotaxonomic marker of the genus Roccella. Five of these compounds were evaluated for their cytotoxic activities against four cancer cell lines. Only orsellinylmontagnetol A exerted a moderate activity against MCF-7 cell line with an IC value of 68.39 ± 3.46 μM.

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Section: Resultsmentioning

confidence: 74%