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Articles tagged with: Epoxide

Still In The RBF »

[4 Sep 2011 | 64 Comments | 21,464 views]
Maoecrystal Z

Reisman, Cha, Yeoman. J. Am. Chem. Soc, 2011, ASAP. DOI: 10.1021/ja2073356 
A busy couple of weeks in the Reisman lab, it appears – really nice syntheses of the Cepharatines and 8-Demethoxyrunanine in Angewandte (doi: 10.1002/anie.201104487), but I decided to blog this tasty synthesis of Maoecrystal Z.  Of course, this isn’t the first member of that family that I’e blogged – the seminal synthesis of Maoecrystal V made my December 2010 column in Chemistry World.  I remember when I wrote that piece that the pseudo-3D structure used to represent the target annoyed …

Still In The RBF »

[10 Aug 2009 | 36 Comments | 13,864 views]
Dioxepandehydrothyrsiferol

Jamison, Tanuwidjaja, Ng. JACS, 2009, ASAP. DOI: 10.1021/ja9052366.
Capitalising upon his pontifications analyses in Science (2007), Tim Jamison has come-up with the goods; a poly-epoxide cascade to build a poly-ether.  He’s not the only one – Frank McDonald crafted a nice synthesis last year using the same principles.  However, Jamison has upped the epoxide count, controlling formation of three ether rings in one go.
As ever, the initial trial is construction of the linear, poly-epoxy precursor – with few surprises in Jamison’s route.  The starting material is farnesol, …

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[23 Jun 2009 | 46 Comments | 15,347 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 …

Still In The RBF »

[9 Mar 2009 | 14 Comments | 9,707 views]
Omaezakianol

Morimoto, Okita, Kambara. ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200805857.
This isn’t the first poly-THF we’ve examined at Tot. Syn., but it is the most complex (see sylvaticin back in 2006 for the other example).  To the casual eye, the molecule looks deceptively symmetrical, but it isn’t.  In fact, only the two right-most THFs are alike, with the others differing in substitution, making the synthesis considerably more complex.  And to be frank, that’s the only reason we’re looking at it, as there doesn’t appear to be any biological activity.  …