A concise total synthesis of DL-histrionicotoxin

The synthesis of (+/-)-histrionicotoxin has been achieved in just nine steps using a two-directional synthesis strategy. Key reactions include a two-directional cross-metathesis, a tandem oxime formation/Michael addition/1,4-prototopic shift/[3 + 2]-cycloaddition cascade, a selective Z,Z-bisenyne formation, and a one-pot N-O and bischloroacetylene reduction.     

A concise total synthesis of salinosporamide A

A concise and straightforward 14-step total synthesis of (+/-)-salinosporamide A, based on a diastereoselective acid-catalysed intramolecular cyclisation of to the pyrrolidinone , and a regioselective reduction of the malonate derivative 8b to the aldehyde 9, is described.     

A concise total synthesis of naamidine A

[reaction: see text]. A total synthesis of naamidine A is reported. Key benefits of the described pathway include its brevity, its synthetic ease, and its flexibility with respect to the preparation of analogues. Formation of the 2-aminoimidazole core is achieved by condensation of the appropriate alpha-aminoketone with cyanamide.     

A concise total synthesis of bruceolline E

An efficient synthesis of bruceolline E was completed in three steps from the known ethyl indole-1-carboxylate (9d) in 60% overall yield, via a tandem acylation/Nazarov cyclization with 3,3-dimethyl acrylic acid followed by selenium dioxide oxidation to install the α-diketone functionality.     

A concise total synthesis of melithiazole C

A short and convergent synthesis of the myxobacterial antibiotic melithiazole C is described featuring a highly E-selective cross-metathesis as the key step.     

A concise asymmetric total synthesis of aspidophytine

An expedient asymmetric total synthesis of aspidophytine is reported. A highly convergent strategy involving the sequential annulation of vinyl iodide 5 with indole 6 exploits varying modes of indole reactivity to provide aspidophytine in 23% over six steps from 5.     

A diastereoselective and concise synthesis of functionalised vinyl epoxides with a Morita-Baylis-Hillman backbone

A highly diastereoselective organocatalytic synthesis of unique functionalised vinyl epoxides, displaying a Morita-Baylis-Hillman backbone, has been developed by means of an user friendly sulfonium ylide epoxidation of aldehydes from a readily available alpha-(bromomethyl)acrylamide derivative. The first result in the asymmetric version is discussed.     

A concise and stereoselective total synthesis of L-783,290

A stereoselective total synthesis of L-783,290 has been achieved involving Alder–Rickert reaction, ring closing metathesis, and chemoselective oxidation as key steps. This approach has successfully demonstrated a linear sequence of reactions, which are highly stereoselective for the construction of the resorcylic acid unit.     

A concise, convergent total synthesis of monocerin

A concise and convergent eight-step synthesis of the antifungal metabolite monocerin 1 is reported. The key step involves an allylsilane metathesis/aldehyde condensation sequence to establish the core 2,3,5-trisubstituted tetrahydrofuran. End-game approaches based around intramolecular Heck chemistry revealed an interesting example of formal 6-endo cyclisation, the origin of which was probed using model substrates. The synthesis was ultimately completed by a strategy involving stepwise oxidative cleavage of the C3-ethenyl substituent.     

A novel concise total synthesis of (+)-lentiginosine

A total synthesis of (+)-lentiginosine was achieved by using ethyl 3-(pyridin-2-yl)acrylate N-oxide as the starting material and an improved Sharpless asymmetric dihydroxylation as the key step.     

A concise total synthesis of (+)-okaramine C

The first total synthesis of (+)-okaramine C is described. Our previously described selenocyclisation-oxidative deselenation sequence was used to establish a 3a-hydroxy-pyrrolo[2,3-b]indole core, which was modified by selective epimerisation to the common pyrrolo[2,3-b]indole of the okaramines.     

A concise stereoselective total synthesis of Botryolide B

The first total synthesis of Botryolide B is described from easily accessible starting materials. The synthetic strategy involves Jacobsen resolution, Sharpless epoxidation, Swern oxidation, Yamaguchi reaction, and ring closing metathesis (RCM).     

A concise stereoselective total synthesis of (+)-artemisinin

A protective group free, concise, and stereoselective total synthesis of (+)-artemisinin, starting from readily available (R)-(+)-citronellal, is described. Asymmetric 1, 4-addition, Aldol condensation, Ene reaction, regioselective hydroboration are the key steps involved in the total synthesis of the target molecule.     

A concise asymmetric total synthesis of (+)-brevisamide

A new protecting-group-free synthesis of the marine monocyclic ether (+)-brevisamide is reported. The enantioselective synthesis utilizes a key asymmetric Henry reaction and an Achmatowicz rearrangement for the formation of the tetrahydropyran ring. A penultimate Stille cross-coupling allows for an efficient installation of the conjugated (E,E)-diene side chain ultimately delivering (+)-brevisamide.     

A concise first total synthesis of narceine imide

A concise and efficient total synthesis of alkaloid narceine imide is disclosed. The key steps are based upon the sequential construction of the isoindolinone template followed by metalation and coupling with an isoquinolinium salt. Subsequent E1cb elimination enables the creation of the arylmethylene unit with the concomitant formation of the dimethylaminoethyl chain and ultimate deprotection completes the synthesis of the natural product.     

A concise, stereocontrolled total synthesis of rippertenol

The first total synthesis of the unique terpene rippertenol, a molecule with dense stereochemical complexity arrayed on a compact framework largely devoid of functional groups, is described. Key elements include orchestrated and unique applications of aldol condensations, Diels-Alder chemistry, and a ring expansion to advance a chiral starting material containing a single chiral center into the final target in a concise and diastereocontrolled manner.