Topic
Total synthesis
About: Total synthesis is a research topic. Over the lifetime, 25578 publications have been published within this topic receiving 489319 citations.
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90 citations
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TL;DR: The total synthesis of (-)-grayanotoxin III (3), a unique tetracyclic diterpene isolated from the leaves of various plants of the family Ericaceae, has been successfully accomplished featuring the highly stereoselective cyclization reactions induced by SmI 2.
Abstract: Total synthesis of (-)-grayanotoxin III (3), a unique tetracyclic diterpene isolated from the leaves of various plants of the family Ericaceae, has been successfully accomplished featuring the highly stereoselective cyclization reactions induced by SmI 2
90 citations
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TL;DR: This report describes in full the total synthesis of the amaryllidaceae alkaloid (+)-plicamine 1 including a model compound study and describes how the compounds were prepared using solid-supported reagents and scavengers in multi-step sequences of reactions to give materials which required no conventional purification but could be carried on to the next synthetic step.
90 citations
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TL;DR: This paper describes a formal total synthesis of the marine ladder toxin hemibrevetoxin B from Danishefsky's dienes by couples the generation of C-glycosides from cyclic enol ethers with metathesis or acid-mediated annulation reactions.
Abstract: This paper describes a formal total synthesis of the marine ladder toxin hemibrevetoxin B from Danishefsky's dienes. This approach couples the generation of C-glycosides from cyclic enol ethers wit...
90 citations
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TL;DR: A concise (nine-step) and effective (19% overall yield) total synthesis of ningalin D is disclosed and is based on a key 1,2,4,5-tetrazine -->1,2-diazine --> pyrrole Diels-Alder strategy to assemble a fully substituted pyr role core central to its structure.
Abstract: A concise (nine-step) and effective (19% overall yield) total synthesis of ningalin D (1a) is disclosed and is based on a key 1,2,4,5-tetrazine --> 1,2-diazine --> pyrrole Diels-Alder strategy to assemble a fully substituted pyrrole core central to its structure. Additional highlights of the synthesis include a double Dieckmann condensation to introduce the C and D aryl rings enlisting substituents judiciously placed on the dienophile and intrinsic to the widely used tetrazine 2, a highly effective Suzuki coupling of the resulting C and D phenol triflates for introduction of the sterically demanding F and G aryl rings, and an unusually effective formal oxidative decarboxylation reaction cascade initiated by a Curtius rearrangement to directly provide the biphenylene quinone methide found imbedded in the structure of ningalin D. The cytotoxic and multidrug resistance (MDR) reversal activity of ningalin D, its derivatives, and the key synthetic intermediates are detailed.
90 citations