A Concise and Modular Synthesis of Pyranicin
- 10 October 2008
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (21) , 4955-4957
- https://doi.org/10.1021/ol802041c
Abstract
A modular, 13-step synthesis of the tetrahydropyran-containing annonaceous acetogenin pyranicin is reported. Key features are the use of an Achmatowicz oxidation-Kishi reduction sequence for the assembly of a pyranone from a furan and the application of Fu's alkyl-alkyl Suzuki coupling for subunit union.This publication has 29 references indexed in Scilit:
- Synthesis of pyranicin and its deoxygenated analogues and their inhibitory action with bovine heart mitochondrial complex ITetrahedron, 2008
- Origin of Stereoselectivity in the Reduction of a Planar OxacarbeniumOrganic Letters, 2008
- Synthesis of Pyranicin and Its Inhibitory Action with Bovine Heart Mitochondrial Complex IOrganic Letters, 2008
- Highly Functionalized Pyranopyrans from Furans: A Synthesis of the C27−C38 and C44−C53 Subunits of Norhalichondrin BOrganic Letters, 2007
- Divergence en Route to Nonclassical Annonaceous Acetogenins. Synthesis of Pyranicin and PyragonicinThe Journal of Organic Chemistry, 2006
- Titanium(II)-Mediated Cyclizations of (Silyloxy)enynes: A Total Synthesis of (−)-7-Demethylpiericidin A1Journal of the American Chemical Society, 2005
- Acetogenins from Annonaceae: recent progress in isolation, synthesis and mechanisms of actionNatural Product Reports, 2005
- Total Synthesis of PyranicinOrganic Letters, 2004
- Total Synthesis of a Cytotoxic Acetogenin, PyranicinOrganic Letters, 2003
- Unusual bioactive annonaceous acetogenins from Goniothalamus giganteusTetrahedron, 1998