-
12
-
-
0003796326
-
-
The absolute (3S,4R)-configuration of (+)-pilocarpine 1 was established in 1966, see:
-
The absolute (3S,4R)-configuration of (+)-pilocarpine 1 was established in 1966, see:. Hill R.K., and Barcza S. Tetrahedron 22 (1966) 2889
-
(1966)
Tetrahedron
, vol.22
, pp. 2889
-
-
Hill, R.K.1
Barcza, S.2
-
13
-
-
77957059183
-
-
Manske R.H.F., and Holmes H.L. (Eds), Academic, New York, NY
-
Battersby A.R., and Openshaw H.T. In: Manske R.H.F., and Holmes H.L. (Eds). The Alkaloids Vol. 3 (1953), Academic, New York, NY 201
-
(1953)
The Alkaloids
, vol.3
, pp. 201
-
-
Battersby, A.R.1
Openshaw, H.T.2
-
14
-
-
0000516905
-
-
Brossi A. (Ed), Academic, New York, NY
-
Maat L., and Beyerman H.C. In: Brossi A. (Ed). The Alkaloids Vol. 22 (1983), Academic, New York, NY 281
-
(1983)
The Alkaloids
, vol.22
, pp. 281
-
-
Maat, L.1
Beyerman, H.C.2
-
20
-
-
0003680152
-
-
Gilman A.G., Goodman L.S., and Gilman A. (Eds), Macmillan, New York, NY
-
Talyor P. In: Gilman A.G., Goodman L.S., and Gilman A. (Eds). The Pharmacological Basis of Therapeutics. 6th ed. (1980), Macmillan, New York, NY 96
-
(1980)
The Pharmacological Basis of Therapeutics. 6th ed.
, pp. 96
-
-
Talyor, P.1
-
38
-
-
69049095600
-
-
For additional references related to the synthesis of isopilocarpine 2, see
-
For additional references related to the synthesis of isopilocarpine 2, see:
-
-
-
-
42
-
-
10644249960
-
-
Braun M., Buhne C., Cougali D., Schaper K., and Frank W. Synthesis (2004) 2905
-
(2004)
Synthesis
, pp. 2905
-
-
Braun, M.1
Buhne, C.2
Cougali, D.3
Schaper, K.4
Frank, W.5
-
43
-
-
69049115731
-
-
For additional references related to the syntheses of various analogues, see
-
For additional references related to the syntheses of various analogues, see:
-
-
-
-
51
-
-
69049121742
-
-
2) are generally required for unactivated acetylenes. See:
-
2) are generally required for unactivated acetylenes. See:
-
-
-
-
54
-
-
49249149027
-
-
Newton R.F., Reynolds D.P., Finch M.A.W., Kelly D.R., and Roberts S.M. Tetrahedron Lett. 20 (1979) 3981
-
(1979)
Tetrahedron Lett.
, vol.20
, pp. 3981
-
-
Newton, R.F.1
Reynolds, D.P.2
Finch, M.A.W.3
Kelly, D.R.4
Roberts, S.M.5
-
55
-
-
69049109333
-
-
note
-
Treatment of 9 under these conditions resulted in a change of colour of the solution from deep red to yellow, followed by the formation of a light brown precipitate.
-
-
-
-
56
-
-
69049091449
-
-
note
-
The formation of (E)-α-ethylidene lactone 5 presumably arises from the isomerisation of the initially formed α-vinyl lactone 8, under the influence of the basic imidazole ring.
-
-
-
-
57
-
-
69049114653
-
-
note
-
Since hydrogenation of exclusively (E)-5 gave a 72:28 mixture of pilocarpine 1 and isopilocarpine 2 in quantitative yield, and hydrogenation of an 88:12 mixture of (E)- and (Z)-α-ethylidene lactones 5 (obtained from our first generation racemic synthesis) produced a 70:30 mixture of pilocarpine 1 and isopilocarpine 2 in quantitative yield; this indicates that the double bond geometry within 5 does not have a major impact on the product distributions obtained.
-
-
-
-
58
-
-
69049108052
-
-
note
-
An authentic sample of (+)-pilocarpine 1 was kindly supplied by Macfarlan Smith Ltd., Edinburgh; base-catalysed epimerisation of this sample also provided a diastereoisomerically pure sample of (+)-isopilocarpine 2.
-
-
-
-
59
-
-
69049106013
-
-
For reviews, see
-
For reviews, see:
-
-
-
-
63
-
-
69049112405
-
-
For a comprehensive review of the use of lipases as biocatalysts in organic solvents, see
-
For a comprehensive review of the use of lipases as biocatalysts in organic solvents, see:
-
-
-
-
65
-
-
45249126845
-
-
Ader U., Breitgoff D., Klein P., Laumen K.E., and Schneider M.P. Tetrahedron Lett. 30 (1989) 1793
-
(1989)
Tetrahedron Lett.
, vol.30
, pp. 1793
-
-
Ader, U.1
Breitgoff, D.2
Klein, P.3
Laumen, K.E.4
Schneider, M.P.5
-
67
-
-
69049093350
-
-
note
-
1H NMR spectroscopy with chiral shift reagents were unsuccessful, however conversion of 25 to its Mosher's ester derivative enabled ee determination, see Ref. 9 within.
-
-
-
-
70
-
-
69049090383
-
-
note
-
3, and comparison with an authentic racemic sample.
-
-
-
-
74
-
-
69049108242
-
-
note
-
3N complete racemisation of monoacetate 29 was observed after only 48 h.
-
-
-
-
75
-
-
69049110459
-
-
note
-
1H NMR spectrum of the crude reaction mixture and pure product.
-
-
-
-
76
-
-
69049118705
-
-
note
-
2, CO (1 atm), 20 °C, 17 h.
-
-
-
-
82
-
-
69049118704
-
-
note
-
2 are added, see Ref. 26 within.
-
-
-
-
83
-
-
69049119784
-
-
note
-
2 at 50 atm pressure in MeOH, giving a 72:28 mixture of 1:2, respectively. Interestingly Pearlman's catalyst showed a small preference for formation of isopilocarpine 2 (56:44 mixture).
-
-
-
-
85
-
-
49149123176
-
-
Chemical Crystallography Laboratory, University of Oxford, UK
-
Betteridge P.W., Carruthers J.R., Cooper R.I., Prout C.K., and Watkin D.J. Crystals (2001), Chemical Crystallography Laboratory, University of Oxford, UK
-
(2001)
Crystals
-
-
Betteridge, P.W.1
Carruthers, J.R.2
Cooper, R.I.3
Prout, C.K.4
Watkin, D.J.5
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