A catalytic asymmetric total synthesis of (−)-perophoramidine
نویسندگان
چکیده
منابع مشابه
A catalytic asymmetric total synthesis of (−)-perophoramidine
We report a catalytic asymmetric total synthesis of the ascidian natural product perophoramidine. The synthesis employs a molybdenum-catalyzed asymmetric allylic alkylation of an oxindole nucleophile and a monosubstituted allylic electrophile as a key asymmetric step. The enantioenriched oxindole product from this transformation contains vicinal quaternary and tertiary stereocenters, and is obt...
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Described in this report is the first total synthesis of elatol, a halogenated sesquiterpene in the chamigrene natural product family. The key disconnections in our synthetic approach include an enantioselective decarboxylative allylation to form the all-carbon quaternary stereocenter and a ring-closing olefin metathesis to concomitantly form the spirocyclic core as well as the fully substitute...
متن کاملTotal synthesis of (+)-perophoramidine and determination of the absolute configuration.
The first asymmetric total synthesis of (+)-perophoramidine has been achieved in 17 steps with ∼11% overall yield. The key step relies on an asymmetric biomimetic Diels-Alder reaction between the in situ-generated chiral diene T-24 and the substituted tryptamine 23 to assemble the core structure 27a in a highly efficient way. An acid-catalyzed thermodynamic equilibrium results in C═N double-bon...
متن کاملCatalytic Asymmetric Synthesis
Course objectives: At the end of this course you should be able to: • Recognise the types of functional groups which can be prepared by catalytic asymmetric methods discussed in the course; • Use this knowledge in planning the synthesis of enantiomerically enriched compounds from given prochiral starting materials; • Outline the scope and limitations of any methods you propose, with respect to ...
متن کاملCatalytic asymmetric synthesis
Three researchers share this years’ Nobel Prize in Chemistry; Dr William S. Knowles, who has been working at Monsanto Company, St Louis, USA; Professor Ryoji Noyori, Nagoya University, Chikusa, Nagoya, Japan and Professor K. Barry Sharpless, The Scripps Research Institute, La Jolla, California, USA. The Royal Swedish Academy of Sciences rewards the three chemists for: ”their development of cata...
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ژورنال
عنوان ژورنال: Chemical Science
سال: 2015
ISSN: 2041-6520,2041-6539
DOI: 10.1039/c4sc01826e