Synthesis of (+)-complanadine A, an inducer of neurotrophic factor excretion.
A total synthesis of the Lycopodium alkaloid (+)-complanadine A is described. Complanadine A has been shown to induce the secretion of neurotrophic factors from 1321N1 cells, promoting the differentiation of PC-12 cells. The use of a simplifying metal mediated [2+2+2] + [2+2+2] sequence using a silyl-substituted diyne and 2 equiv of the corresponding alkyne-nitrile has provided rapid access to the natural product.
Yuan
Changxia
C
Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712, USA.
Chang
Chih-Tsung
CT
Axelrod
Abram
A
Siegel
Dionicio
D
D000818:Animals; D002454:Cell Differentiation; D002478:Cells, Cultured; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000494:pharmacology; D032502:Lycopodium / Q000378:metabolism*; D009414:Nerve Growth Factors / Q000378:metabolism*; D009457:Neuroglia / Q000187:drug effects / Q000378:metabolism; D051381:Rats
D006576:Heterocyclic Compounds, 4 or More Rings; D009414:Nerve Growth Factors; C550939:complanadine A