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Articles tagged with: macrolactone

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[11 Oct 2009 | 36 Comments | 15,833 views]
Aigialomycin D

Barrett, Calo, Richardson. Org. Lett., 2009, ASAP. DOI: 10.1021/ol901979x.
Macrolactones?  From Barrett?  It’s not his usual fayre, but as is more normal, there is a twist in the synthesis.  I think most chemists (or at least me…), when presented with a target like aigialomycin, would think about buying-in the aromatic portion, and then trying to bolt on the styrene-type olefin and building around.  However, with his interests in reactive intermediates, Tony Barrett (of IC, London… just down the road), it comes of no real surprise to me that he …

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[23 Jun 2009 | 46 Comments | 15,584 views]
Gloeosporone

Jamison, Trenkle. ACIEE, 2009, ASAP. DOI: 10.1002/anie.200902079.
When a target’s been made as many times as gloeosporone, it’s a good idea to come along with something new.  And when the people you’re following have a bit of a rep, it makes it doubly necessary.  How does Seebach (twice), Fürstner, Schreiber, Ley and Holmes make you feel?  Good thing Tim Jamison’s got quite a thing for a macrocycle, and an impressive creativity with them – as demonstrated in his synthesis of acutiphycin, covered here back in 2006.  He’s …

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[28 Feb 2009 | 21 Comments | 17,250 views]
Sporolide B

Nicolaou, Tang, Wang. ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200900264.
The second of two papers published (almost) in succession in Angewandte from the KCN labs (also check out some more methodology in JACS – nice to see more methods from his group), sporolide B is the more challenging target, but devoid of any biological activity.  Nicolaou justifies his synthesis by discussing the biosynthetic origins of the sporolides, which are potentially products of enediyne cyclisation.  Convinced?  Perhaps…
Anyway, the structure is certainly interesting, being one of relatively few natural products that …

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[16 Feb 2009 | 17 Comments | 12,446 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…)?

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[16 Apr 2008 | 43 Comments | 12,697 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 …

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[6 Apr 2008 | 26 Comments | 12,047 views]

MacMillan, Carpenter, Northrup, Chung, Wiener and Kim, ACIEE, 2008, EarlyView. DOI: 10.1002/anie.200800086.
Macrolide time again, and as this is David MacMillan, proline time too. The callipeltoside family of natural products has been reasonably popular, with syntheses from the usual suspects: Trost, Evans, Paterson, and Panek. However, all of those syntheses were of callipeltoside A, so this synthesis marks the first of callipeltoside C, including a reassignment of stereochemistry (the sugar fragment needed all is stereocenters inverted). Retro:

So far reasonably predictable/sensible disconnection – and you’ll note no …

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[13 Mar 2008 | 30 Comments | 14,178 views]

Paterson, Anderson, Dalby, Lim, Genovino, Maltas, and Moessner.ACIEE, 2008, EarlyView. DOIs: 10.1002/anie.200705565, 10.1002/anie.200705566.
Now I’ve been waiting for this ‘un… those of you who have been reading for a while will remember that I used to study at Cambridge University, and shared weekly meetings with the Paterson group. It’s certainly an ambitious target, with 21 stereocenters – and when they started the work, the absolute stereochemistry was yet to be assigned! Plenty of other groups are working on a synthesis of this beast, including …

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[3 Mar 2008 | 10 Comments | 6,423 views]

Nicolaou, Chen, Guduru, Sun, and Banerji. ACIEE, 2007, EarlyView. DOI: 10.1002/anie.200702243 JACS, 2008, ASAP. DOI: 10.1021/ja710485n.
You’d be forgiven for a feeling of déjà vu when looking at the post – yes, you have seen it before. Originally described in an Angewandte paper last year (which was discussed on this blog), Nicolaou and Chen achieved a smart, logical synthesis of the marine macrolide. The main problem was not the synthesis (which, at least from their description, was achieved without adversity), but the stereochemistry. The stereochemical …