The presence of eucalyptol in Artemisia australis validates its use in traditional Hawaiian medicine.

OBJECTIVE: To identify the major organic compounds of Artemisia australis (A. australis), a plant used in traditional Hawaiian medicine for the treatment of asthma. METHODS: The dichloromethane extract of A. australis was analyzed by gas chromatography-mass spectroscopy and major compounds were identified by a National Institute of Standards and Technology library search and confirmed by peak enhancement. RESULTS: The major chemical components of A. australis include eucalyptol, borneol, and caryophyllene. CONCLUSIONS: The presence and biological activity of eucalyptol correlate very well with the usage of this plant in traditional Hawaiian medicine.

Expanding the repertoire of natural product-inspired ring pairs for molecular recognition of DNA.

A furan amino acid, inspired by the recently discovered proximicin natural products, was incorporated into the scaffold of a DNA-binding hairpin polyamide. While unpaired oligomers of 2,4-disubstituted furan amino acids show poor DNA-binding activity, furan (Fn) carboxamides paired with N-methylpyrrole (Py) and N-methylimidazole (Im) rings demonstrate excellent stabilization of duplex DNA as well as discrimination of noncognate sequences, consistent with function as a Py mimic according to the Py/Im polyamide pairing rules.

Synthetic Studies Towards the Mitomycins: Construction of the Tetracyclic Core via a Reductive Aminocyclization Reaction.

The tetracyclic core of the mitomycin family of natural products has been formed in one step from an acyclic precursor via a reductive aminocyclization reaction. Additionally, the 8-membered benzazocine can be prepared without the need for prior activation of the aniline. Construction of a mitomycin K analogue lacking the C9a methoxy moiety is also reported herein.

Synthetic and biosynthetic studies on FR900482 and mitomycin C: an efficient and stereoselective hydroxymethylation of an advanced benzazocane intermediate.

We report a simple, efficient, and stereoselective Mukaiyama aldol approach to install the key hydroxymethyl moiety into the benzazocane framework of FR900482. Synthetic investigations revealed that the reaction is highly dependent upon the electronics of the aromatic ring. This approach enabled the economical introduction of a [13C] label to study the biosynthesis of these structurally and biogenetically related natural products. Epimerization of the initially formed beta-hydroxy ketone may enable access to mitomycin C or FR900482 biosynthetic congeners.