<oai_dc:dc xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:oai_dc="http://www.openarchives.org/OAI/2.0/oai_dc/" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xsi:schemaLocation="http://www.openarchives.org/OAI/2.0/oai_dc/ http://www.openarchives.org/OAI/2.0/oai_dc.xsd">
  <dc:creator>Piemontesi C</dc:creator>
  <dc:creator>Wang Q</dc:creator>
  <dc:creator>Zhu J</dc:creator>
  <dc:date>2016</dc:date>
  <dc:description xmlns:ns0="xml" ns0:lang="en">A gram-scale enantioselective total synthesis of (+)-peganumine A was accomplished in 7 steps from commercially available 6-methoxytryptamine. Key steps included (a) a Liebeskind-Srogl cross-coupling; (b) a one-pot construction of the tetracyclic skeleton from an ω-isocyano-γ-oxo-aldehyde via a sequence of an unprecedented C-C bond forming lactamization and a transannular condensation; (c) a one-pot organocatalytic process merging two achiral building blocks into an octacyclic structure via a sequence of enantioselective Pictet-Spengler reaction followed by a transannular cyclization. This last reaction created two spirocycles and a 2,7-diazabicyclo[2.2.1]heptan-3-one unit with excellent control of both the absolute and relative stereochemistry of the two newly created quaternary stereocenters.</dc:description>
  <dc:identifier>https://sonar.ch/global/documents/166438</dc:identifier>
  <dc:language>eng</dc:language>
  <dc:relation>info:eu-repo/semantics/altIdentifier/doi/10.1021/jacs.6b07846</dc:relation>
  <dc:relation>info:eu-repo/semantics/altIdentifier/pmid/27558528</dc:relation>
  <dc:source>Journal of the American Chemical Society. - 2016</dc:source>
  <dc:subject xmlns:ns1="xml" ns1:lang="en">Carbolines</dc:subject>
  <dc:subject xmlns:ns2="xml" ns2:lang="en">Carboxylic Acids</dc:subject>
  <dc:subject xmlns:ns3="xml" ns3:lang="en">Catalysis</dc:subject>
  <dc:subject xmlns:ns4="xml" ns4:lang="en">Chemistry Techniques, Synthetic</dc:subject>
  <dc:subject xmlns:ns5="xml" ns5:lang="en">Stereoisomerism</dc:subject>
  <dc:title xmlns:ns6="xml" ns6:lang="en">Enantioselective Synthesis of (+)-Peganumine A.</dc:title>
  <dc:type>http://purl.org/coar/resource_type/c_6501</dc:type>
</oai_dc:dc>
