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1
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37049117452
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-
Irie, H.; Masaki, N.; Ohno, R.; Osaki, K.; Taga, T.; Uyeo, S. J. Chem. Soc., Chem. Commun. 1970, 1066.
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(1970)
J. Chem. Soc., Chem. Commun.
, pp. 1066
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-
Irie, H.1
Masaki, N.2
Ohno, R.3
Osaki, K.4
Taga, T.5
Uyeo, S.6
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2
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-
0017882695
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-
Sakata, K.; Aoki, K.; Chang, C.-F.; Sakurai, A.; Tamura, S.; Murakoshi, S. Agric. Biol. Chem. 1978, 42, 457-463.
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(1978)
Agric. Biol. Chem.
, vol.42
, pp. 457-463
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-
Sakata, K.1
Aoki, K.2
Chang, C.-F.3
Sakurai, A.4
Tamura, S.5
Murakoshi, S.6
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5
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-
37049075789
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-
(c) Beddoes, R. L.; Davies, M. P. H.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1992, 538-540.
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(1992)
J. Chem. Soc., Chem. Commun.
, pp. 538-540
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-
Beddoes, R.L.1
Davies, M.P.H.2
Thomas, E.J.3
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9
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0344142416
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note
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1H NMR spectra.
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-
-
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10
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0001544321
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Stevens, R. V.; Chapman, K. T.; Stubbs, C. A.; Tam, W. W.; Albizati, K. F. Tetrahedron Lett. 1982, 4647-4650.
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(1982)
Tetrahedron Lett.
, pp. 4647-4650
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-
Stevens, R.V.1
Chapman, K.T.2
Stubbs, C.A.3
Tam, W.W.4
Albizati, K.F.5
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11
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-
84982490585
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-
(a) Severin, T.; Supp, W.; Manninger, G. Chem. Ber. 1979, 112, 3013-3022.
-
(1979)
Chem. Ber.
, vol.112
, pp. 3013-3022
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-
Severin, T.1
Supp, W.2
Manninger, G.3
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13
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0344142415
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-
note
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4: m/z = 283. Found: mlz = 283.
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-
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16
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0029839528
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(a) Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774-10782.
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(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 10774-10782
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Davies, H.M.L.1
Ahmed, G.2
Churchill, M.R.3
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17
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0021745572
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(b) Ueda, Y.; Roberge, G.; Vinet, V. Can. J. Chem. 1984, 62, 2936-2940.
-
(1984)
Can. J. Chem.
, vol.62
, pp. 2936-2940
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-
Ueda, Y.1
Roberge, G.2
Vinet, V.3
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19
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0345435988
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note
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+).
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-
-
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20
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0345435987
-
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note
-
Alkylation of 12 was attempted with LiHMDS, LDA, and KHMDS with allyl iodide. The only products isolated were axial and equatorial C-allylation products at the methylene distal to the n-butyl group.
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-
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22
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0345435985
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(b) For stereochemical rationale, please see: Fleming, I.; Kemp-Jones, A. V.; Long, W. E.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 2 1976, 7-14.
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(1976)
J. Chem. Soc., Perkin Trans. 2
, pp. 7-14
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Fleming, I.1
Kemp-Jones, A.V.2
Long, W.E.3
Thomas, E.J.4
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23
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33947462653
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Pappo, R.; Allen, Jr., D. S.; Lemieux, R. U.; Johnson, W. S. J. Org. Chem. 1956, 21, 478-479.
-
(1956)
J. Org. Chem.
, vol.21
, pp. 478-479
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Pappo, R.1
Allen D.S., Jr.2
Lemieux, R.U.3
Johnson, W.S.4
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25
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0039081687
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Ogilvie, K. K.; Thompson, E. A.; Quilliam, M. A.; Westmore, J. B. Tetrahedron Lett. 1974, 2865-2868.
-
(1974)
Tetrahedron Lett.
, pp. 2865-2868
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-
Ogilvie, K.K.1
Thompson, E.A.2
Quilliam, M.A.3
Westmore, J.B.4
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27
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0344573827
-
-
note
-
The stereochemistry about the methyl center was determined from the X-ray crystal structure of pentacyclic lactone 24. The structure revealed the methyl group to be equatorial as in the natural product. Homonuclear decoupling of the methyl group revealed a coupling constant J = 11.3 Hz between the bridgehead proton and the methine proton, further confirming the assigned stereochemistry.
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-
28
-
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0344142414
-
-
note
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Molecular modeling suggested that the α,β-unsaturated ketone should be oriented to preferentially allow attack from the bottom face of the alkene. The steric bulk of the TIPS protecting group may also have helped direct the approach of the nucleophile from the bottom face.
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-
-
-
29
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0344142413
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note
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+).
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31
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85008039425
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Ishizumi, K.; Koga, K.; Yamada, S. I. Chem. Pharm. Bull. 1968, 16, 492-497.
-
(1968)
Chem. Pharm. Bull.
, vol.16
, pp. 492-497
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-
Ishizumi, K.1
Koga, K.2
Yamada, S.I.3
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33
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37049072174
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(a) Pelter, A.; Al-Bayati, R. I. H.; Ayoub, M. T.; Lewis, W.; Pardasani, P.; Hansel, R. J. Chem. Soc., Perkin Trans. 1 1987, 717-742.
-
(1987)
J. Chem. Soc., Perkin Trans. 1
, pp. 717-742
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Pelter, A.1
Al-Bayati, R.I.H.2
Ayoub, M.T.3
Lewis, W.4
Pardasani, P.5
Hansel, R.6
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34
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37049130804
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(b) Knight, D. W.; Pattenden, G. J. Chem. Soc., Perkin Trans, 1 1975, 635-640.
-
(1975)
J. Chem. Soc., Perkin Trans, 1
, pp. 635-640
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Knight, D.W.1
Pattenden, G.2
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35
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0345435982
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note
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5 or Burgess reagent gave no reaction. Direct addition of the lithium enolate of the butenolide to lactone 24 was unsuccessful; the retro-aldol equilibrium favors the lactone 24.
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-
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-
36
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-
0345004870
-
-
note
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2.
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