Linked Life Data

19681075

Source:http://linkedlifedata.com/resource/pubmed/id/19681075

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
38
pubmed:dateCreated
2009-9-28
pubmed:abstractText
Homo- and heterodimeric bispyrrolidinoindoline diketopiperazine alkaloids have been synthesized following a concise, versatile, and stereoselective route. Highlights of the sequence are a diastereoselective construction of the C3a-bromo-hexahydropyrrolo[2,3-b]indole nucleus, its Co(I)-induced C3a-C3a' dimerization, and the twofold or sequential amide-bond formation before cyclization to the diketopiperazine of the homo- or heterodimeric alkaloids, respectively. Stereochemical diversity is achieved through the choice of the appropriate amino acids combined with the base-induced epimerization of the C2-acyl-hexahydropyrrolo[2,3-b]indole at C2. According to this strategy, the natural products (+)-WIN 64821 1, (+)-WIN 64745 2 and (+)-asperdimin 6 as well as analogues (5, 22, 32, 44) with different relative and absolute configuration have been efficiently synthesized. The flexibility of this synthetic methodology has facilitated the structural revision of the natural product (+)-asperdimin, whose structure has been corrected to diastereomer 6.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Sep
pubmed:issn
1521-3765
pubmed:author
pubmed:issnType
Electronic
pubmed:day
28
pubmed:volume
15
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
9928-37
pubmed:meshHeading
pubmed:year
2009
pubmed:articleTitle
Stereocontrolled and versatile total synthesis of bispyrrolidinoindoline diketopiperazine alkaloids: structural revision of the fungal isolate (+)-asperdimin.
pubmed:affiliation
Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, As Lagoas/Marcosende, 36310 Vigo, Spain.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't