Total Synthesis of Serofendic Acids A and B Employing Tin-Free Homoallyl−Homoallyl Radical Rearrangement
- 2 August 2005
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (18) , 3929-3932
- https://doi.org/10.1021/ol051411t
Abstract
Total syntheses of serofendic acids A (1a) and B (1b) are described. The key strategic element of the approach involves the novel tin-free homoallyl-homoallyl radical rearrangement of 5 for the construction of bicyclo[2.2.2]octane ring system 4. In addition, the conversion of methyl atisirenoate 2 to serofendic acids A (1a) and B (1b) was achieved on the basis of the Michael reaction of sodium thiomethoxide.[reaction: see text]Keywords
This publication has 11 references indexed in Scilit:
- Synthesis and absolute configuration of serofendic acidsTetrahedron Letters, 2002
- Isolation of a diterpenoid substance with potent neuroprotective activity from fetal calf serumProceedings of the National Academy of Sciences, 2002
- Remarkable Control of Radical Cyclization Processes of Cyclic Enyne: Total Syntheses of (±)-Methyl Gummiferolate, (±)-Methyl 7β-Hydroxykaurenoate, and (±)-Methyl 7-Oxokaurenoate and Formal Synthesis of (±)-Gibberellin A12 from a Common Synthetic PrecursorJournal of the American Chemical Society, 2001
- First Total Synthesis of (±)-Methyl Gummiferolate Using a Homoallyl−Homoallyl Radical Rearrangement ReactionOrganic Letters, 1999
- Construction of bicyclo[2.2.2]octane ring system via homoallyl-homoallyl radical rearrangementTetrahedron Letters, 1999
- Flight from the Tyranny of Tin: The Quest for Practical Radical Sources Free from Metal EncumbrancesAngewandte Chemie International Edition in English, 1998
- Total Synthesis of (±)-Methyl Atis-16-en-19-oate via Homoallyl−Homoallyl Radical RearrangementJournal of the American Chemical Society, 1998
- Novel Catalysis by N-Hydroxyphthalimide in the Oxidation of Organic Substrates by Molecular OxygenThe Journal of Organic Chemistry, 1995
- Direct synthesis of Z-unsaturated esters. A useful modification of the horner-emmons olefination.Tetrahedron Letters, 1983
- Sulfur trioxide in the oxidation of alcohols by dimethyl sulfoxideJournal of the American Chemical Society, 1967