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Chemistry World February 28, 2013 Paul Docherty |
Lyconadin A Since its isolation from the clubmoss Lycopodium complanatum in 2001, lyconadina A has been party to three total syntheses. All that interest stems from anti-Alzheimer's activity attributed to the lycopodium family. |
Chemistry World March 2012 Paul Docherty |
Column: Totally Synthetic Ring strain is a fascinating phenomenon - one that is best understood with plastic modelling kits, wearing safety specs for ring sizes of four or less. |
Chemistry World April 2012 Paul Docherty |
Column: Totally Synthetic Detecting rearrangements still seems like an abstract ability for aspiring synthetic chemists. Erick Carreira's synthesis of indoxamycin B is a great case in point, employing two rearrangement reactions. |
Chemistry World February 2011 Paul Docherty |
Column: Totally Synthetic Although most of the natural products I've discussed have had biological activity at the core of the rationale for their synthesis, most organic chemists will admit that an unusual chemical structure is by far the stronger draw. |
Chemistry World January 29, 2014 |
Organic matter: Indoxamycins A, C and F In 2012, Erick Carreira's group in Zurich reported the total synthesis of indoxamycin B. 1 This 24-step organometallic tour de force resulted in a structural reassignment and set the bar rather high for future work on this family. |
Chemistry World July 30, 2013 Paul Docherty |
Melotenine A Chirality, where would we be without you? Often the bane of the synthetic chemist's life, the challenge of asymmetry is perhaps what makes total synthesis so endlessly intriguing. |
Chemistry World April 2010 Paul Docherty |
Column: Totally Synthetic When one attempts the first synthesis of a natural product, the set of challenges are often unknown; which intermediates are either inaccessible or unstable, for instance. |
Chemistry World October 2008 Paul Docherty |
Column: Totally Synthetic Samuel Danishefsky of Columbia University (and the Sloan-Kettering Institute for cancer research), has focused on function rather than family. His many synthetic conquests are unified by their cancer-busting potential. |
Chemistry World June 2011 |
Column: Totally Synthetic I've never heard of the Polonovski-Potier reaction, the keystone of a remarkable synthesis by a team led by Tohru Fukuyama at the University of Tokyo, Japan. |
Chemistry World July 1, 2012 Paul Docherty |
Vincorine Cage-structured natural products are some of the most appealing (if perhaps not appetising) targets for organic chemists -- perhaps due to their obvious intricacy of form, but also because of their structural rigidity. |
Chemistry World November 2, 2015 |
Batzelladine B Of all the diverse substances that nature produces, the alkaloids -- small molecules containing basic nitrogen -- have had the greatest impact on human history and health. |
Chemistry World April 2009 Paul Docherty |
Column: Totally Synthetic Perhaps the most frustrating part of being a synthetic chemist is the jealousy with which we must regard nature |
Chemistry World August 2009 Paul Docherty |
Column: Totally Synthetic Richmond Sarpong's research group at University of California, Berkeley, US, have taken quite an interest in lyconadin A, publishing an initial, racemic synthesis. |
Chemistry World February 2010 Paul Docherty |
Column: Totally Synthetic Palau'amine is an alkaloid which has stubbornly held off synthesis for over 15 years. Its nemesis comes in the form of Phil Baran at the Scripps Research Institute, La Jolla, US. |
Chemistry World November 5, 2013 Paul Docherty |
Marcfortines B & C Natural product isolation is generally a tale of a journey to an obscure or inaccessible location, followed by pulping a harmless plant or marine sponge to get at compounds made by some bacteria hiding out in the core. |
Chemistry World October 29, 2014 |
Lycopodium alkaloids Not all natural products are created equal. A glance at the total synthesis literature from the past decade is enough to discover that some molecules attract a lot more attention than others. |
Chemistry World February 2012 Paul Docherty |
Column: Totally Synthetic Medium rings are a beguiling feature found in a host of natural products, owing to their behavioral oddities. |
Chemistry World January 2, 2013 Paul Docherty |
Flueggine A One of the most prolific sources of biologically active natural products is traditional medicines -- whose active components can be exceptionally potent. The Euphorbiaceae family of plants is a productive source of medicinal targets, including the Securinega alkaloids. |
Chemistry World May 2012 Paul Docherty |
Column: Totally Synthetic Hopeanol and hopeahainol A |
Chemistry World November 27, 2012 Paul Docherty |
Pentalenolactone A methyl ester One team that really gets the Pauson -- Khand reaction or the PKR and all its nuances is that led by Zhen Yang at Peking University in Beijing, China. They recently published a very neat synthesis of the intricate pentalenolactone |
Chemistry World July 2010 Paul Docherty |
Column: Totally Synthetic Isolated in 1986, the steroid family of aplykurodinones have shown selective cytotoxicity in a variety of cancer cell lines, and add to the phenomenal list of steroids with potent medicinal properties. |
Chemistry World January 2010 Paul Docherty |
Column: Totally Synthetic Of all the natural product classes, the steroid family are perhaps the most prevalent in the public consciousness; from cholesterol to testosterone, their infamy inflates the 'science bit' in countless advertisements. |
Chemistry World May 29, 2013 Paul Docherty |
Pactamycin A member of a 'rival' field stating that a molecule is 'inaccessible by synthetic organic chemistry' is like a red rag to the proverbial bull. This challenge surrounds analogs of pactamycin, a complex cyclopentane-based target with an exceptionally potent biological profile. |
Chemistry World June 2010 Paul Docherty |
Column: Totally Synthetic Although its chemistry is mature and varied, my use of silicon reagents in my synthetic forays has been limited to a somewhat clumsy use of hydroxyl protecting groups. |
Chemistry World September 2, 2013 Paul Docherty |
Steviol A discussion is presented on new ways to synthesize the diterpenoid steviol. |
Chemistry World August 2011 Paul Docherty |
Column: Totally Synthetic Yuanhuapin, a fabulously complex member of the daphnane diterpene orthoester class of natural products, bears an astonishing twelve contiguous stereogenic centres around its seven rings (look closely!). |
Chemistry World November 2010 Paul Docherty |
Column: Totally Synthetic Perhaps the most familiar (and dull - they do say that familiarity breeds contempt.) chemical reaction to medicinal chemists is the amide bond formation. |
Chemistry World April 2011 Paul Docherty |
Column: Totally Synthetic Reactions in the synthesis of guanacastepene N. Discovered in fungi growing on trees in the Guanacaste conservation area in Costa Rica, several syntheses of this family have appeared in the decade since their isolation. |
Chemistry World June 2009 Paul Docherty |
Column: Totally Synthetic With potent bacteria-beating activity, it's no surprise that kendomycin has recently grabbed quite a bit of attention. |
Chemistry World October 2010 Paul Docherty |
Barekoxide and barekol Like most scientists, organic chemists can often obsess about a problem, endlessly pursuing the perfect yield or enantioselectivity, often leading to tears and broken glassware. |
Chemistry World July 2008 Paul Docherty |
Column: Totally Synthetic The target is hypocrellin A, which couldn't look much less like last month's callipeltoside A. Even a casual glance reveals one intriguing feature of this target - the fact it exists in equilibrium with an isomer. |
Chemistry World February 2009 Paul Docherty |
Column: Totally Synthetic The farming squeeze has renewed interest in compounds with anti-insect abilities, especially those known for their activity against specific pests. |
Chemistry World October 2009 Paul Docherty |
Column: Totally Synthetic It's been a while since I've seen such a battle for the 'first publication' of a molecule as has recently been witnessed for haplophytine. |
Chemistry World December 17, 2009 Simon Hadlington |
Single catalyst gives two products from racemic mixture Chemists in the US have demonstrated a remarkable reaction in which a single catalyst can transform a racemic mixture - molecules identical in every way except for their chirality - into two distinct enantiomerically pure products. |
Chemistry World November 2008 Paul Docherty |
Column: Totally Synthetic Vannusal B -- This is a classic case of misassigned identity - the structure published by the researchers who first isolated the compound from its natural source has been recreated via total synthesis, and found wanting. |
Chemistry World May 2011 Paul Docherty |
Column: Totally Synthetic The ability to understand molecular structure is perhaps both our greatest skill and largest encumbrance as scientists. A quick glance at the structure of a target such as nanolobatolide tells us much about its connectivity and the manner in which it might react. |
Chemistry World June 27, 2013 Paul Docherty |
Bolivianine The still-growing and insanely diverse class of terpene natural products is probably responsible for a considerable number of undergraduate headaches. |
Chemistry World August 30, 2009 Phillip Broadwith |
C-H oxidation proves its worth US researchers are going against the grain of total synthesis and developing new approaches to complex molecules. |
Chemistry World January 2009 Paul Docherty |
Column: Totally Synthetic In the search for new biologically active natural products, sometimes a team isolating a new compound family will be lucky enough to find one active member. |
Chemistry World January 28, 2015 |
Rubriflordilactone A It's likely that organic chemists have been practicing retrosynthesis in one form or another for at least a century, and certainly for decades before E J Corey formalized the concept in the mid-1990s |
Chemistry World August 2010 Paul Docherty |
Column: Totally Synthetic The total synthesis of macrolide targets is now a relatively mature field. Any synthesis that bucks these trends grabs attention, with a recent publication of dictyosphaeric acid A by Richard Taylor's team at the University of York, UK, a case in point. |
Chemistry World July 30, 2014 |
Psylloborine A It's a somewhat surprising assertion that almost a fifth of natural products are thought to include a dimerization step somewhere in their biosynthesis. |
Chemistry World December 2009 Paul Docherty |
Column: Totally Synthetic What turns a good synthesis into a great synthesis are the steps surrounding that motif, something that Darren Dixon from the University of Oxford, UK, exemplifies with this synthesis of Nakadomarin A. |
Chemistry World July 3, 2015 Andy Extance |
Copper catalysis overcomes double bond trouble Some carbon-carbon double bonds seem too unreactive for synthetic use -- but that's just how chemists in the US are now exploiting them. |
Chemistry World January 2011 Paul Docherty |
Column: Totally Synthetic Although the story is incomplete, the target is a worthy challenge - leiodolides A and B have powerful activity and selectivity against NI60 tumour cells, and may lead to therapeutic agents. |
Chemistry World May 2010 Paul Docherty |
Column: Totally Synthetic In the case of englerin A, the synthetic strategies used by Dawei Ma's group at the Chinese Academy of Sciences, Shanghai, China, 1 and Antonio Echavarren's team at Rovira and Virgili University, Tarragona, Spain, 2 are extremely similar. |
Chemistry World September 2010 Paul Docherty |
Column: Totally Synthetic After a target has been synthesised, and the question of 'can we make this?' has been answered, perhaps the most important remaining question is 'how did nature make it?' |
Chemistry World March 2009 Paul Docherty |
Column: Totally Synthetic Marine waters have produced some of the biggest celebrities of the natural product world - including the brevitoxins, saxitoxins and tetrodotoxins, 1 famous as much for the sheer human effort needed for their landmark syntheses as for their complexity and size. |
Chemistry World July 27, 2015 |
(--)-Jiadifenolide I believe that Ryan Shenvi's could well be the last synthesis we see of the popular neurotrophic agent jiadifenolide, at least for some time. |
Chemistry World November 16, 2012 Yuandi Li |
(+)-Myrrhanol C made Spanish chemists have completed the stereospecific total synthesis of (+)-myrrhanol C. This compound is a natural triterpene isolated from mastic gum, a substance well known for its medicinal properties as well as use in various cuisines. |