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Still In The RBF »

[16 Feb 2009 | 17 Comments | 12,442 views]
Norhalichondrin B Pt. I

Phillips, Jackson, Henderson, Motoyoshi. ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200806111. Article PDF Supporting Information Group Website

As I said in the last post, it was a rather quiet fortnight for total synthesis, at least as the big journals go. However, I think Andy Phillips can feel justified in his absence when he’s been cooking molecules like this ‘un up. Norhalichondrin B is part of the halichondrin family, isolated about twenty years ago – plenty of time for a bit of synthetic action, kicked off by Kishi back in ’92. Impressively, the synthesis hasn’t been entirely academic, with the peeps at Eisai Pharma also working on analogues. So how to start (lots of grant-application forms…)?

Still In The RBF »

[20 Apr 2008 | 29 Comments | 8,544 views]

Toste, Radosevich, Chan and Shih, ACIEE, 2008, EarlyView. DOI: 10.1002/anie.200800554.
Another paper from the Toste group that doesn’t use recycled Rolex watches in any of the steps. Indeed, the metal of choice today is vandadium – read-up on the methodology in this tasty JACS from 2005. Anyway, the target is octalactin A, a medium ring lactone with a bit of murine melanoma and colon tumor busting activity. Previous syntheses by Buszek, Clardy, Shiina and my boss with Andy Holmes, so it’s certainly seen …

Still In The RBF »

[16 Apr 2008 | 43 Comments | 12,691 views]

Roulland, ACIEE, 2008, EarlyView. DOI: 10.1002/anie.200800585.
Yep, just one name. And an impressive synthesis for just one chap (and I don’t think he even had the backing of “Bioic Bros. GMBH” like La Clair). Even the target has more names – this one was independantly isolated three times, gaining haterumalide NA and FR177391as alternative monikers (albeit with different optical rotations…). No mention is made of its biological profile in this paper, but a synthesis of the methyl ester by Snider in 2003 states “Haterumalide …