29329-03-1Relevant articles and documents
A short, efficient route of 1-hydroxylated vitamin D ring A fragments
Mascarenas,Garcia,Castedo,Mourino
, p. 4365 - 4368 (1992)
The bis-exocyclic conjugated diene system of vitamin D ring A synthons is efficiently constructed by means of a palladium-catalyzed intramolecular cyclization of the (Z)-iodoalkene resulting from the stereoselective hydrometallation-iodinolysis of proparg
Intramolecular Alkyne Carbomercuration by Allylic Silanes: A New Carbon-Carbon Bond-Forming Reaction
Huang, He,Forsyth, Craig J.
, p. 8595 - 8596 (1997)
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Palladium-catalyzed intramolecular iodine-transfer reactions in the presence of β-hydrogen atoms
Monks, Brendan M.,Cook, Silas P.
, p. 14214 - 14218 (2013)
Atom economy: A palladium-catalyzed atom-transfer reaction of secondary alkyl iodides is described. An intramolecular double insertion of an alkyne and olefin provides access to primary iodides possessing β-hydrogen atoms. The process delivers these complex bicyclic homoallylic iodides with tetrasubstituted olefins from easily accessible aliphatic iodides. Different functional groups, including common heterocycles, are tolerated. Copyright
Polymer supported cobalt carbonyl complexes as novel traceless alkyne linkers for solid-phase synthesis
Comely, Alex C.,Gibson, Susan E.,Hales, Neil J.
, p. 2075 - 2076 (1999)
The immobilisation of functionalised alkynes onto 'polymer-bound triphenylphosphine', their chemical manipulation and subsequent release has been demonstrated for the first time, thus illustrating that cobalt carbonyl complexes can be used as 'traceless' π-alkyne linkers.
A Ring Closing Metathesis Approach to the Formal Synthesis of (+)-Callyspongiolide
Ko, Kwang-Yoon,Wilson, Zoe E.,Furkert, Daniel P.,Brimble, Margaret A.
, p. 5759 - 5771 (2020)
An enantioselective synthesis of macrocyclic core of (+)-callyspongiolide is described, constituting a formal synthesis of this natural product. The synthetic strategy constructs the 14-membered macrocyclic domain via Yamaguchi esterification followed by a challenging ring-closing metathesis (RCM) to effect the final formation of the macrolactone.
Synthesis of the C1-C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments
Anderson, Edward A.,Bernasconi, Alice,Blanco, Araceli,Challis, Gregory L.,Chintalapudi, Venkaiah,Gudmundsson, Haraldur G.,Lim, Jieyan,Song, Lijiang,Tran, Minh
supporting information, p. 7439 - 7444 (2021/10/01)
The stambomycins are a family of bioactive macrolides isolated from Streptomyces ambofaciens. Aside from two stereocenters installed through cytochrome P450 oxidations, their stereochemistry has been predicted by sequence analysis of the polyketide synthase. We report a synthesis of the C1-C27 fragment of stambomycin D, the spectroscopic data of which correlates well with that of the natural product, further validating predictive sequence analysis as a powerful tool for stereochemical assignment of complex polyketide natural products.
Anodic Oxidation of Aminotetrazoles: A Mild and Safe Route to Isocyanides
Leech, Matthew C.,Petti, Alessia,Tanbouza, Nour,Mastrodonato, Andrea,Goodall, Iain C. A.,Ollevier, Thierry,Dobbs, Adrian P.,Lam, Kevin
supporting information, p. 9371 - 9375 (2021/12/09)
A new electrochemical method for the preparation of isocyanides from easily accessible aminotetrazole derivatives has been developed, which tolerates an unprecedented range of functional groups. The use of chemical, rather than electrochemical, oxidation to afford isocyanides was also demonstrated, which provides access to these compounds for those without electrosynthesis equipment. The practicality of scale-up using flow electrochemistry has been demonstrated, in addition to the possibility of using electrochemically generated isocyanides in further reactions.
