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	<title>TotallySynthetic.com</title>
	<link>http://totallysynthetic.com/blog</link>
	<description>4,512 Ph. D. students died to make this blog...</description>
	<lastBuildDate>Mon, 08 Feb 2010 21:41:40 +0000</lastBuildDate>
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	<item>
		<title>Phostriecin and/or Sultriecin</title>
		<description><![CDATA[
Boger, Burke, Haq.  JACS, 2010, ASAP. DOI: 10.1021/ja9097252.   
Figured it out already?  I bet it caused a few scratched-heads in Dale Boger&#8217;s group when, having made the published structure for Sultriecin, things didn&#8217;t tally-up.  We&#8217;ve discussed quite a few reassignments here over the years, but the majority are antipodal stereoclusters, or isomerisations at worst.  In this case, even the molecular formula was wrong!  The group may well have been suspicious before this point, though, as the related fostriecin, cytostatin and phospholine all contain the phosphate-mono ester that ...]]></description>
		<link>http://totallysynthetic.com/blog/?p=2277</link>
			</item>
	<item>
		<title>Crambidine</title>
		<description><![CDATA[
Gin, Perl, Ide, Prajapati, Perfect, Duron.  JACS, 2010, ASAP. DOI: 10.1021/ja910831k.   
When I see targets containing guanidine moieties these days, I immediately think of David Gin, which goes to show how much he owns that motif just now.  Looking back into the murky past of Tot Syn, an earlier post covered Gin&#8217;s synthesis of Batzelladine A, which was fairly guanidine-tastic.  This bad-boy only has one, but with a bit of &#8220;anticancer, anti-HIV, antifungal, and Ca2+ ion channel blocking [activity]&#8220;, that grant-form presumably filled itself, especially at MSKCC.  However, ...]]></description>
		<link>http://totallysynthetic.com/blog/?p=2264</link>
			</item>
	<item>
		<title>Hyperforin</title>
		<description><![CDATA[
Shibasaki, Kanai, Shimizu, Shi, Usuda.  ACIEE, 2010, EarlyView. DOI: 10.1002/anie.200906678.  ; Shibasaki, Kanai, Kuramochi, Usuda. Org. Lett., 2004, 6, 4387. DOI: 10.1021/ol048018s.   
Three amazingly tough targets completed in (almost) as many months &#8211; you can&#8217;t tell me that total synthesis is stifled.  Hyperforin has been staining the white-boards of many a lab for decades &#8211; the isolation (reported in Antibiotik&#8230;) was way back in &#8216;71, and has resisted synthesis until now.  Shibasaki himself has been working on it for quite a while, as you&#8217;ll have seen in the header &#8211; a key ...]]></description>
		<link>http://totallysynthetic.com/blog/?p=2248</link>
			</item>
	<item>
		<title>Piperkadsin C [Isolation] &#8211; Updated</title>
		<description><![CDATA[
Lee, Kim, Choi, Ha, Kim. BOMCL, 2010, 20, 409-412. DOI: 10.1016/j.bmcl.2009.10.016.   
The Tot. Syn. bull-shit detector is at eleven just now, having just read Derek Lowe&#8217;s post on Piperkadsin C.  This natural product was isolated by Kang Ro Lee of Sungkyunkwan University in a assay-guided chromatographic separation of isolates from Piper kadsura (Piperaceae).  It doesn&#8217;t take much more than a glance to see that something seems very wrong with this structure, as it seems to contain a bridged cyclobutene, partially containing a dieneone.  From a chemical stability aspect, this is scary enough, ...]]></description>
		<link>http://totallysynthetic.com/blog/?p=2236</link>
			</item>
	<item>
		<title>Isatisine A</title>
		<description><![CDATA[
Kerr, Karadeolian.  ACIEE, 2010, EarlyView. DOI: 10.1002/anie.200906632.   
It&#8217;s always going to be a tough situation for the article I blog following something like Palau&#8217;amine, but this short and sweet synthesis by Michael Kerr of the University of Western Ontario (in the other London &#8211; which I visited in &#8216;95) is as good as can be.  The rationale for it&#8217;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 ...]]></description>
		<link>http://totallysynthetic.com/blog/?p=2232</link>
			</item>
	<item>
		<title>Palau&#8217;amine</title>
		<description><![CDATA[
Baran, Seiple, Su, Young, Lewis and Yamaguchi.  ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200907112.  
Y&#8217;know, I was kinda hoping for a bit of break between blog-posts this winter, as the amount of online publications tends to tail-off around the year-end.  However, not only have the publications been thick-&#8217;n'-fast (got quite a lot of material to get through), but up pops palau&#8217;amine.  I really did think that Angewandte would hold-off until sometime in early 2010, but here it is &#8211; and it lives up to Baran&#8217;s reputation.  I mean that in ...]]></description>
		<link>http://totallysynthetic.com/blog/?p=2213</link>
			</item>
	<item>
		<title>(iso)Bongkrekic Acid</title>
		<description><![CDATA[
Ley, Francais, Leyva, Etxebarria-Jardi. Org. Lett., 2009, ASAP. DOI: 10.1021/ol902676t.   
For those UKian readers out there, there&#8217;s a fittingness to my posting a Cambridge paper following an Oxford last week.  Having spent a bit of time at both, it&#8217;s hard for me to pick a particular allegience, but I guess I have to go light blue, and congratulate the boys for their dug-in performance at Twickenham a few weeks back.  But I am particularly lucky to have been at both, as their approach to organic chemistry was so markedly different. ...]]></description>
		<link>http://totallysynthetic.com/blog/?p=2187</link>
			</item>
	<item>
		<title>1-Deoxynojirimycin and 1-Deoxyaltronojirimycin</title>
		<description><![CDATA[
Davies, Bagal, Lee, Roberts, Russell, Scott, Thomson. Org. Lett., 2009, ASAP. DOI: 10.1021/ol902533b.   
More of a post-ette than a full post, this tasty little nugget was found buried amongst effective reposts and updates.  Out there to give you a freaky sense of de ja vous are full papers on kendomycin, spirastrellolide, nakiterpiosin&#8230; finding something new was an effort!
What we&#8217;ve got here are a pair of closely related synthese of some poly hydroxylated piperidenes; notable for their glycosidase inhibitory effects.  Huh, I hear you say (actually, probably not &#8211; there are ...]]></description>
		<link>http://totallysynthetic.com/blog/?p=2178</link>
			</item>
	<item>
		<title>Nakadomarin A</title>
		<description><![CDATA[
Yeah, I&#8217;ve not posted in a bit&#8230; Cephalostatin 1 is going into Chemistry World next month, but this months is also worth a read.  Darren Dixon&#8217;s synthesis of Nakadomarin A contains quite a few interesting transformation, and is very succinct.
]]></description>
		<link>http://totallysynthetic.com/blog/?p=2172</link>
			</item>
	<item>
		<title>9-Isocyanopupukeanane</title>
		<description><![CDATA[
Corey, Brown. Org. Lett., 2009, ASAP. DOI: 10.1021/ol9025793.  . Corey, Behforouz, Ishiguro. JACS., 1979, 101, 1608–1609. DOI: 10.1021/ja00500a048.   
Again, it&#8217;s been a while since I blogged, and this time the excuses are two-fold.  First of all, I moved home recently to the leafy London suburb of Surbiton (saaf-wess, for natives&#8230;), and have been without my computer, interweb access and beer, all three of which are required for blogging.  However, more critically, there&#8217;s been a real dearth of total synthesis in the ASAPs, so much so that this paper isn&#8217;t even a formal synthesis (not in the title at ...]]></description>
		<link>http://totallysynthetic.com/blog/?p=2160</link>
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