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Articles tagged with: THF

Still In The RBF »

[10 Jan 2010 | 17 Comments | 14,163 views]
Isatisine A

Kerr, Karadeolian. ACIEE, 2010, EarlyView. DOI: 10.1002/anie.200906632.
It’s always going to be a tough situation for the article I blog following something like Palau’amine, but this short and sweet synthesis by Michael Kerr of the University of Western Ontario (in the other London – which I visited in ’95) is as good as can be.  The rationale for it’s investigation is also pertinant, as it turns out that Isatisine A is a moderately active HIV isolate (EC50 of 38 ?m).  A secondary interest in the isolation was …

Still In The RBF »

[10 Aug 2009 | 36 Comments | 14,070 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, …

Still In The RBF »

[9 Mar 2009 | 14 Comments | 9,863 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.  …