@article{be5273212c7643a799c93874158b05d7,
title = "Electrooxidative synthesis of morphinandienones from 1-benzyltetrahydroisoquinolines",
abstract = "The electrochemical oxidation of several 1-benzyl tetrahydroisoquinolines has been performed at a platinum anode in acetonitrile. Using potentiostatic conditions and a three compartment cell, the following cyclizations were accomplished on a several hundred milligram scale in the yields indicated: 6′-bromolaudanosine to O-methylflavinantine (16%), 5′-methoxylaudanosine to O-methyl-C-norandrocymbine (38%), 8-methoxylaudanosine to protostephanone (35%), norlaudanosine to N-nor-O-methylflavinantine (22%).",
author = "Falck, {J R} and Miller, {L. L.} and Stermitz, {F. R.}",
note = "Funding Information: REFERENCES {\textquoteleft}This work was supportedi n part by researchg rantG M-19234fr om the National Institute of General Medical Sciences,N IH. LLM is an Alfred P. Sloan Fellow and JRF was a National Science FoundationT rainee {\textquoteleft}L. L. Miller, F. R. Stermitz and J. R. Falck, 1. Am. Chem. Sot. 93, 5941( 1971) {\textquoteleft}L. L. Miller. F. R. Stermitza ndJ . R. Falck. Ibid. 95.265I (1973) T. Kametani, M. Koizumi and K. Fukumoto, Chem. Pharm. Bull. 17, I&?9 (1%9) {\textquoteleft}A. R. Battersby,A . K: Bhatnagar,P . Hackett, C. W. Thornbera ndJ . Staunton,C hem.C ommun 1214(1 968) 6R.N elson, CollecGon of Czech Communications 36,842 (~~1) {\textquoteleft}C. K. Mann and K. K. Barnes, Hectrochemical Reoc- tions in Nonaqueous Systems Chap. 9. Marcel Dekker, New York, N.Y., (1970) “J. M. Bobbitt and R. C. Hallcher, Chem. Commun. 543 (191) vE. Splth and N. Lang, Ber. Dtsch. Chem. Ges. 54.3064 (1921) {\textquoteleft}“G. Goldschmiedt.M onalsh. 667 (1885) “T. Vitali and L. Chierci, Chimica. Milan 7, 409 (1952); Chem. Abstr. 48. 2076d (1954) “C. Schiipf and i. Thierfelde;, L&b@ Ann. 537. 143 (1939) “M. Tomita, M. Kozuka and S. Vyeo, YakugakuZ asshi 86, 460 (1966);C hem. Abstr. 65, 10634(1 966) {\textquoteleft}T. Kametani, T. Sugaharaa nd K. Fukumoto. Chep. Pharm. Bull. 17, 1809( 1969) “NMR and IR spectra of the authentic sample were kindly provided by Prof. T. Kametani. “We thank Mr. Michael Harlow for performing this analysis “R. F. Nystrom, J. Am. Chem. Sot. 77, 2544( 1955) {\textquoteleft}“r. Kametania nd K. Ohkubo, Yakuguku Zosshi 89,279 (1969);C hem. Abstr. 70, 106356(l %9) {\textquoteleft}B. Franck andG . Blaschke,L iebigs Ann. 695. I44 (1966) me NMR and IR spectrao f the authentics amplew ere kindly provided by Professor A. R. Battersby “K. W. Bentley and A. W. Murray, 3. Chem. Sot. 2497 (l%3) ?. Baxter,L . T. AIlan andG . A. Swan, Ibid 3645( 1965) “T. H. Yang and C. M. Chen, /. Chim. Chem.S ot. Taipei l7, 54 (1970) “Y. Inubushi, Y. Aoyagi and M. Matsuo, Tetrahedron Letters 2363 (1%9)",
year = "1974",
doi = "10.1016/S0040-4020(01)97477-0",
language = "English (US)",
volume = "30",
pages = "931--934",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "8",
}