2 research outputs found
Total Synthesis of (−)-Bicubebin A, B, (+)-Bicubebin C and Structural Reassignment of (−)-<i>cis</i>-Cubebin
The
first total synthesis of (−)-bicubebin A, and two previously
unreported dilignans, (−)-bicubebin B and (+)-bicubebin C has
been achieved through the dimerization of (−)-cubebin, confirming
the structure and absolute stereochemistry of (−)-bicubebin
A. Analysis of the data for (−)-bicubebin B showed it matched
that of reported compound (−)-<i>cis</i>-cubebin.
The NMR data of the subsequently synthesized proposed structure of <i>cis</i>-cubebin confirmed that its original proposed structure
was incorrect
Biologically Active Acetylenic Amino Alcohol and <i>N</i>‑Hydroxylated 1,2,3,4-Tetrahydro-β-carboline Constituents of the New Zealand Ascidian <i>Pseudodistoma opacum</i>
The first occurrence of an acetylenic
1-amino-2-alcohol, distaminolyne
A (<b>1</b>), isolated from the New Zealand ascidian <i>Pseudodistoma opacum</i>, is reported. The isolation and structure
elucidation of <b>1</b> and assignment of absolute configuration
using the exciton coupled circular dichroism technique are described.
In addition, a new N-9 hydroxy analogue (<b>2</b>) of the known <i>P. opacum</i> metabolite 7-bromohomotrypargine is also reported.
Antimicrobial screening identified modest activity of <b>1</b> toward <i>Escherichia coli</i>, <i>Staphylococcus
aureus</i>, and <i>Mycobacterim tuberculosis</i>, while <b>2</b> exhibited a moderate antimalarial activity (IC<sub>50</sub> 3.82 μM) toward a chloroquine-resistant strain (FcB1) of <i>Plasmodium falciparum</i>