Philip Morris
Synthesis and Biological Characterization of Pyridohomotropanes. Structure-Activity Relationships of Conformationally Restricted Nicotinoids
Fields
- Author
- Abood, L.G.
- Kanne, D.B.
- Area
- CENTRAL FILES/PRE-DB WAREHOUSE
- Type
- SCRT, REPORT, SCIENTIFIC
- BIBL, BIBLIOGRAPHY
- CHAR, CHART, GRAPH, TABLE, MAPS
- BIBL, BIBLIOGRAPHY
- Site
- R107
- Named Person
- Ashworth, D.
- Broadhurst, M.D.
- Callahan, W.
- Chavdarian, C.G.
- Cheng, M.
- Pearlman
- Broadhurst, M.D.
- Request
- Stmn/R1-078
- Stmn/R1-147
- Document File
- 2021576679/2021576983a/Missing
- 2021576680/2021576983/870000
- Named Organization
- New England Nuclear
- Author (Organization)
- Stauffer Chemical
- Univ of Rochester
- Litigation
- Stmn/Produced
- Master ID
- 2021576754/6831
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- Date Loaded
- 05 Jun 1998
- UCSF Legacy ID
- bkr44e00
Document Images
11
c. Spivak, C.E.; Witkop, B. Albuquerque, E.X. Mol. Pharmacol. 1980, 18,384.
d. Eldefrawi, M.E.; Abalis, I.M.; Sherby, S.M.; Eldefrawi, A.T. Ch. 9 from
Neuropharmacology and Pesticide Action Edited by Ford, M.G.; Lunt, G.G.;
Reay, R.C.; Usherwood, P.N.R.
14. House, H.O.; Bare, T.M. J. Org. Chem. 1968, 33,946.
15. Hu, M.W.; Bondinell, W.E.; Hoffman, D. J. Labelled Compd. 1974, 10, 79.
16a. Bates, H.A.; Rappoport, H. J. Am. Chem. Soc. 1979, 101, 1259.
b. Peterson, J.S.; Fels, G.; Rapoport, H. J. Am. Chem. Soc. 1984, 106, 4539.
c. Peterson, J.S.; Toteberg-Kaulen, Sabine; Rapoport, H. J. Org. Chem.
1984, 49, 2948.
d. Koskinen, A.M.P.; Rapoport, H. J. Med. Chem. 1985, 28, 1301.
12
Experimental conditions sunmary for Scheme 1.
a) 4 Equiv. Benzylamine, MeOH, 72°C, 100 hr; 86%; b) 1 eq. Hg(OAc)2, THF, 4°C,
1.5 hr., NaOH, NaBH4; 70%; c) Jone's oxidati'on; 45%; d) KH, Et3B, allyl bro-
mide, THF, 0-25°C; 75%; e) 2 equiv Tos Mic, 5 equiv. potassium tert-butoxide,
DME, 45°C; 74%; f) MeLI, ether, Ax; 64%; g) 2 equiv DIBAL; benzene, 25°C, 5h;
75%; h) 03, CH2C12, -78°C, dimethylsulfide; 1) 3 equiv. NH2OH-HC1, gl HOAC,
100°C, 20 min; 12 was produced in 39% yield over two steps (h and i); J)
H2-Pd(OH)2/C, 1 equiv HC1, EtOH; 3b was produced in 71% yield; k) 37% HCHO, gl
HOAc, NaCNBH3; 58%.
17
la RCH3:. Nicotine
Ib R-H: Nornicotina
2 Acetylcholine
R=
3a RI-R2rH: Pyrid*o(3,4-b)hoaotropane (PHT)
3b RI-CH3 Rp-H: 2'-Methyl-PHT
3c RI-H R2-CH3 : H-llethyl-PHT
4a a-c.ia-Anatozin-a
4b a-traaa-Anatoxin-a
