Last month’s article focused on marinomycin, a cyclic polyketal with rather obvious symmetry – and the synthetic strategy hinged on that feature. However, symmetry in natural products isn’t always so apparent and it is uncovering such ‘hidden symmetry’ that forms the core of this month’s column.

Again, we’re plunging into the marine depths to find natural products with prodigious biological activity. The amphidinolide family comprises over 30 members, varying in architecture but (almost) all featuring a complex and highly decorated macrolactone ring at the core. Amphidinolide F was first isolated in 1991, but as yet remains unconquered territory in synthetic laboratories.^1,2However, new ground has been broken by a pair of chemists from Oregon State University, US, led by Rich Carter.³ Their key insight was that hidden symmetry exists in the complex tetrahydrofuran (THF) regions. Although these two regions are not identical, the team considered that enough chemistry was in common that a mutual precursor might be used.  More…

‘Ultramarine blue is a colour illustrious, beautiful, and most perfect, beyond all other colours’, wrote the Italian artist Cennino Cennini in the late 14th century. He and his contemporaries adored this mineral pigment for its rich, deep lustre. But they didn’t use it much, at least not unless they had a particularly wealthy client, because it was very costly. As the name implies, it came from ‘over the seas’ – all the way from what is now Afghanistan, where mines in the remote region of Badakhshan were the only known source of the parent mineral, lapis lazuli, for centuries. Not only was ultramarine expensive to import, but it was laborious to make: repeatedly grinding and washing the raw material to separate the blue colourant. Ultramarine could cost more than its weight in gold, and so painters reserved it for the most precious parts of their altarpieces, especially the robes of the Virgin Mary.  More…

Faculty Development: Applications for the L.L. Stewart Faculty Development Fund are due Oct.31. The L.L. Stewart Faculty Development Fund provides individual faculty members with grants of up to $2,200 for professional development activities that have a clear connection to the enhancement of teaching and student learning at OSU. Beginning this year, up to two grants for $4,400 may also be considered for exceptionally compelling and well-written proposals. Academic advising-related proposals are welcome. Applications and guidelines are available at: http://oregonstate.edu/ctl/grants