STEREOSELECTIVE TOTAL SYNTHESES OF (±)-RECIFEIOLIDE AND (R)-(+)-RICINELAIDIC ACID LACTONE
- 5 August 1977
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 6 (8) , 959-962
- https://doi.org/10.1246/cl.1977.959
Abstract
The naturally occurring macrolide, (±)-recifeiolide, was synthesized stereoselectively. (E)-11-Hydroxy-8-dodecenoic acid (5) was obtained stereoselectively from 11-hydroxy-8-dodecynoic acid by the reduction with lithium, and the acid (5) was cyclized to (±)-recifeiolide in excellent yield via its 6-phenyl-2-pyridyl ester. Similarly, (R)-(+)-ricinelaidic acid was lactonized to afford the corresponding lactone in high yield.Keywords
This publication has 7 references indexed in Scilit:
- Synthese des (R)‐trans‐11‐Hydroxy‐8‐dodecensäure‐lactons (Recieifeiolid)Helvetica Chimica Acta, 1976
- A stereoselective synthesis of (+-)-11-hydroxy-trans-8-dodecenoic acid lactone, a naturally occurring macrolide from Cephalosporium recifeiJournal of the American Chemical Society, 1976
- 11-Hydroxy-trans-8-dodecenoic Acid Lactone, a 12-Membered-Ring Compound from a FungusCanadian Journal of Chemistry, 1971
- Improved procedure for oxidations with the chromium trioxide-pyridine complexThe Journal of Organic Chemistry, 1970
- Germinal Organometallic Compounds. I. The Synthesis and Structure of 1,1-DiborohexaneJournal of the American Chemical Society, 1967
- Toxic Fluorine Compounds. XVIII.1 The Synthesis of the Toxic Principle of Dichapetalum toxicarium (18-Fluoro-cis-9-octadecenoic Acid) and Related ω-Fluoro Unsaturated Acids2,3Journal of the American Chemical Society, 1963
- The Cleavage of Tetrahydropyran by Acid Chlorides in the Presence of Zinc Chloride. The Preparation of 5-Diethylaminopentanol-1Journal of the American Chemical Society, 1947