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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 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 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 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 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 September 2008 Paul Docherty |
Column: Totally Synthetic The need to discover new antibiotics to treat resistant strains of bacteria is a well- documented and discussed challenge for chemists. |
Chemistry World November 2011 Paul Docherty |
Column: Totally Synthetic Gelsemoxonine has an extra four-membered azetidine ring, making for a considerable synthetic challenge. |
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 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 September 2, 2013 Paul Docherty |
Steviol A discussion is presented on new ways to synthesize the diterpenoid steviol. |
Chemistry World July 2009 Paul Docherty |
Column: Totally Synthetic When it comes to making large natural products, different researchers will often propose identical 'end-game' strategies to complete the target. |
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 July 9, 2012 Phillip Broadwith |
'Molecular cobra' turns C-H to C=C A reagent developed by US chemists can selectively introduce synthetically useful C=C double bonds into unactivated carbon chains, guided by an activating group attached to a nearby oxygen or nitrogen atom. |
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 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 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 December 2010 Paul Docherty |
Column: Totally Synthetic In a conversation at the beginning of this year, a friend and I considered the most challenging targets available to the total-synthesizer - and maoecrystal V was at the top of the list. |
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 October 31, 2012 Paul Docherty |
Epicoccin G The class of natural products known as 2,5-diketopiperazines is both broad and synthetically well-trodden. An important sub-class of these targets are found with a sprinkling of sulfur atoms, and seem particularly well-suited to pathogen-bashing. |
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 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 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 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 August 2008 Paul Docherty |
Column: Totally Synthetic Impersonating nature isn't easy, and biomimetic syntheses are remarkable in two senses. |
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 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 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 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 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 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 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 May 2009 Paul Docherty |
Column: Totally Synthetic After a glorious 1980s and 90s as the pin-ups of total synthesis, it seems that the macrolides are now passe, and all the cool kids have moved on to work on alkaloid natural products |
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 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 February 19, 2010 Simon Hadlington |
Forcing stereoselectivity on reactive cations Chemists in the US have devised a dual catalyst strategy to tame the highly reactive iminium ion to give a high degree of stereochemical control over subsequent reactions of the ion. |
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 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 December 2008 Paul Docherty |
Column: Totally Synthetic Pseudolaric acid B: regular readers of this column's online incarnation will have noticed that this is the second appearance for this particular synthesis. |
Chemistry World October 1, 2012 Paul Docherty |
Prostaglandin F2I There's been no shortage of grant funding for synthetic chemistry of the prostaglandins, keeping some of the finest minds in organic chemistry engaged over the last five decades. |
Chemistry World June 1, 2012 Paul Docherty |
atrop-Abyssomicin C This member of the abyssomicin family is the only one to achieve bacteria-bashing prowess, and is also the only one to feature atropisomerism -- a relatively unusual form of stereoisomerism in naturally occurring species |
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 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 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 February 27, 2012 Phillip Broadwith |
Bending carbonyl reactivity rules Belgian chemists have uncovered a method to bypass the standard reactivity hierarchy of carbonyl compounds, allowing a ketone or ester to be reduced in the presence of a more reactive aldehyde. |
Chemistry World July 2011 Paul Docherty |
Column: Totally Synthetic At first glance rippertenol looks a mere hop-skip-and-jump from its parent. However, a more careful examination reveals a stray methyl group at C1, complicating the synthesis of an already tricky target. |
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 November 3, 2008 Simon Hadlington |
Organic synthesis set for auto-pilot Peptides are routinely made by machines that couple together amino acid components. Could organic synthesis ever get this simple? |
Chemistry World July 27, 2009 Simon Hadlington |
Peer review by live blogging Blogging can immediately bring together expert opinion on a given topic. Poorly reviewed papers claiming novelty can be expected to be rapidly dissected in the blogosphere, as some chemists have found out. |