Highly Stereoselective Total Syntheses of 2,5‐Anhydro‐4‐deoxy‐D‐ribo‐hexonic Acid and of (1S)‐1‐C‐(6‐amino‐7H‐purin‐8‐yl)‐1,4‐anhydro‐3‐deoxy‐D‐erythro‐pentitol (= cordycepin C)
- 15 March 1989
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 72 (2) , 271-277
- https://doi.org/10.1002/hlca.19890720211
Abstract
Highly regio‐ and stereoselective monohydroxylation of the CC bond of (+)‐7‐oxabicyclo[2.2.1]hept‐5‐en‐2‐one (8) was achieved via LiAlH4 reduction of the corresponding 5,6‐exo‐epoxy dimethyl acetal 9. The reaction gave exclusively (–)‐(1R, 2R, 4S)‐6,6‐dimethoxy‐7‐oxabicyclo[2.2.1]heptan‐2‐exo‐ol (10) which was transformed into 2,5‐anhydro‐3‐O‐benzyl‐4‐deoxy‐D‐ribo‐hexonic acid (15) and 2,5‐anhydro‐4‐deoxy‐D‐ribo‐hexonic acid (6) via ozonolysis of (–)‐(1R, 4S, 6R)‐6‐exo‐benzyloxy‐2‐{[(tert‐butyl)dimethylsilyl]oxy}‐7‐oxabicyclo[2.2.1]hept‐2‐ene (14). Cordycepin C (5) was derived from 6 and 4,5,6‐triaminopyrimidine using CsF/DMF to generate the adenine heterocycle.This publication has 63 references indexed in Scilit:
- Total Synthesis of L‐Allose, L‐Talose, and derivatives.Helvetica Chimica Acta, 1989
- Enantiomerically pure 7‐oxabicylo[2.2.1]hept‐5‐en‐zyl derivatives as synthetic intermediates. Part III. Total synthesis of D‐ and L‐ribose derivativesHelvetica Chimica Acta, 1988
- Acid‐Catalyzed Rearrangements of 5,6‐exo‐Epoxy‐7‐oxabicyclo[2.2.1]hept‐2‐yl Derivatives. Migratory Aptitudes of Acyl vs. Alkyl Groups in Wagner‐Meerwein TranspositionsHelvetica Chimica Acta, 1987
- Syntheses of (+)‐ and (–)‐Methyl 8‐Epinonactate and (+)‐ and (–)‐Methyl NonactateHelvetica Chimica Acta, 1987
- Optical resolution of 7‐oxabicyclo[2.2.1]hept‐21‐ene derivatives. Diastereoselectivity in the formation of cyanohydrine‐brucine complexesHelvetica Chimica Acta, 1984
- The Preparation of Optically Pure 7‐Oxabicyclo [2.2.1]hept‐2‐ene Derivatives. The CD Spectrum of (+)‐(1R)‐7‐Oxabicyclo [2.2.1]hept‐5‐en‐2‐oneHelvetica Chimica Acta, 1983
- Face Selectivity of the Diels‐Alder Additions of Exocyclic Dienes Grafted onto 7‐Oxabicyclo[2.2.1]heptanesHelvetica Chimica Acta, 1982
- Die Diels‐Alder Reaktion von Furan und 2‐Methylfuran mit AcrylnitrilHelvetica Chimica Acta, 1975
- Nuclear magnetic resonance study of exo- and endotricyclo (5.2.1.02,6)deca-3,8-dieneJournal of Magnetic Resonance (1969), 1970
- Nucleic acid components and their analogues. CXVIII. Synthesis of 8-β-D-ribofuranosyladenine starting from 2,5-anhydro-D-allonic acidCollection of Czechoslovak Chemical Communications, 1969