Total Synthesis of (±)-Aplykurodinone-1: Traceless Stereochemical Guidance
- 1 June 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 132 (28) , 9567-9569
- https://doi.org/10.1021/ja1035495
Abstract
The total synthesis of the highly degraded steroidal natural product, aplykurodinone-1 (1), has been accomplished. Key features include a one-flask hydrolysis/retro-aldol/iodolactonization sequence to excise the C8 hydroxymethylene functionality with retention of stereochemistry and the stereoselective installation of the C13 methyl group through hydrogenation with homogeneous catalyst.Keywords
This publication has 45 references indexed in Scilit:
- Pattern Recognition in Retrosynthetic Analysis: Snapshots in Total SynthesisThe Journal of Organic Chemistry, 2007
- Total Synthesis of Antheliolide AJournal of the American Chemical Society, 2006
- Total Synthesis of (−)-Spirotryprostatin B: Synthesis and Related StudiesJournal of the American Chemical Society, 2005
- Enantioselective Total Synthesis of Semperoside AJournal of the American Chemical Society, 2004
- Syntheses of Polycyclic Natural Products Employing the Intramolecular Double Michael ReactionAngewandte Chemie International Edition in English, 1993
- Homogeneous Hydrogenation With Iridium Complexes. Evidence for Polyhydride Intermediates in the Reduction of α-PineneAustralian Journal of Chemistry, 1992
- Michael Addition of Acyclic Lithium 1,3-Dien-2-olates with α,β-Unsaturated Esters, Ketones, and DiestersBulletin of the Chemical Society of Japan, 1991
- Steroids and related natural products. 85. Bufadienolides. 26. Direct conversion of 14-dehydrobufalin to bufalinThe Journal of Organic Chemistry, 1973
- Generation, nuclear magnetic resonance spectra, and alkylation of enolates from trialkylsilyl enol ethersJournal of the American Chemical Society, 1968
- Selective homogeneous hydrogenation of alk-1-enes using hydridocarbonyltris(triphenylphosphine)rhodium(I) as catalystJ. Chem. Soc. A, 1968