Diospyrodin synthesis

Masayuki Inoue and co-workers from the University of Tokyo reported in Organic Letters on the synthesis of diospyrodin.

 

OL paper

The Synthesis of 12alpha-Hydroxy Steroids

Francis Yoshimoto and co-workers at the University of Texas at San Antonio reported in Steroids on the synthesis of 12alpha-hydroxy steroid derivatives to biochemically characterize P450 8B1, the enzyme implicated in cardiovascular health and obesity. Both 7-keto DHEA and 12alpha-hydroxy 7-keto DHEA had antagonistic properties towards the NMDA receptor.

 

Steroids paper

First paper published

Francis Yoshimoto and co-workers at the University of Texas at San Antonio report in the journal, Steroids, on the synthesis of a neurosteroid produced in the brains, 7alpha-hydroxypregnenolone, through an allylic C7-oxidation reaction. The oxidation was performed through either a C7-oxidation through CrO3 in the presence of 3,5-dimethylpyrazole followed by a stereoselective reduction or a regioselective and stereoselective allylic benzoyloxylation using CuBr and tert-butylperoxy benzoate.

Steroids paper

Correlating chemical shift of O-H proton with stereochemistry of masked 1,2-diols

Jason Chen and co-workers from Iowa State have reported in JOC on the chemical shifts of an O-H proton of masked syn- and anti- 1,2-diols.

JOC paper

Mollenynes B-E

Tadeusz Molinski and co-workers have reported in JACS on the isolation and characterization of mollenynes B-E.

JACS paper

Circular dichroism approach to determine chirality

Babak Borhan and co-workers have reported in ACIE on a way to determine remote chirality using the cotton effect and molecular tweezers.

ACIE paper

Stephen Martin and co-workers have reported in JACS on a synthesis of citirnadin A.

JACS paper

Citrinadin B synthesis

John Wood and co-workers at Colorado State University have reported in JACS on a synthesis of citrinadin.

JACS paper

Chlorizidine A

Chambers Hughes and co-workers at Scripps have reported in Organic Letters on the isolation of chlorizidine A, which had low micromolar LC50 values against some cancer cell lines from NCI. Another interesting point in this paper is the way they assigned the chiral carbon stereocenter as S from an X-ray crystal structure of the molecule, which also incorporated a benzene molecule. They determined the stereocenter using the Flack parameter.

OL paper

Flack parameter ref (Acta Cryst)

Carbon-carbon coupling constants for stereochemical determination

R. Thomas Williamson and co-workers at Merck have reported in Organic Letters on the use of DFT to calculate and assign stereochemistry from the C-C coupling constants in NMR.

OL paper