Synthesis of (+)-Complanadine A, an Inducer of Neurotrophic Factor Excretion
- 13 April 2010
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 132 (17), 5924-5925
- https://doi.org/10.1021/ja101956x
Abstract
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.Keywords
This publication has 19 references indexed in Scilit:
- The Lycopodium AlkaloidsHETEROCYCLES, 2009
- Advances in small molecules promoting neurotrophic functionPharmacology & Therapeutics, 2007
- Small Molecule Natural Products in the Discovery of Therapeutic Agents: The Synthesis ConnectionThe Journal of Organic Chemistry, 2006
- A phase 1 clinical trial of nerve growth factor gene therapy for Alzheimer diseaseNature Medicine, 2005
- Complanadine B, obscurumines A and B, new alkaloids from two species of LycopodiumTetrahedron, 2005
- The Lycopodium alkaloidsNatural Product Reports, 2004
- Complanadine A, a new dimeric alkaloid from Lycopodium complanatumTetrahedron Letters, 2000
- A facile synthesis of (-)-R-5-methyl-2-cyclohexen-1-one and related 2-substituted enones from (+)-pulegoneThe Journal of Organic Chemistry, 1984
- Total synthesis of lycopodium alkaloids: (.+-.)-lycopodine, (.+-.)-lycodine, and (.+-.)-lycodolineJournal of the American Chemical Society, 1982
- Total synthesis of (±)-LycodineTetrahedron Letters, 1979