1.Pitiamides A and B, Multifunctional Fatty Acid Amides from Marine Cyanobacteria.
Cai W1, Matthews JH1, Paul VJ2, Luesch H1. Planta Med. 2016 May 2. [Epub ahead of print]
Two geometric isomers related to pitiamide A, termed 1E-pitiamide B (1) and 1Z-pitiamide B (2), were isolated from a marine cyanobacterium collected from the shallow reef flat at Piti Bomb Holes, Guam, Mariana Islands. The structures of these analogues were elucidated using 1D and 2D NMR analysis. Pitiamide A, which has been previously described, but has not been investigated in bioassays, was co-isolated. Pitiamides A and B were subjected to a biological evaluation and they both showed antiproliferative effects on HCT116 cells with IC50 values of 1-5 µM. Pitiamide A was investigated individually and caused plasma membrane hyperpolarization and an increase of intracellular calcium in HCT116 cells.
2.One-Carbon Homologation of Primary Alcohols to Carboxylic Acids, Esters, and Amides via Mitsunobu Reactions with MAC Reagents.
Kagawa N1,2, Nibbs AE3, Rawal VH3. Org Lett. 2016 May 2. [Epub ahead of print]
A method is reported for the one-carbon homologation of an alcohol to the extended carboxylic acid, ester, or amide. The process involves the Mitsunobu reaction with an alkoxymalononitrile followed by unmasking in the presence of a suitable nucleophile. The homologation and unmasking can even be performed in a one-pot process in high yield.
