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Table 2 (continued)
3
4 (yield %)a
Entry
5b
Scheme 2
6b
7b
Scheme 3
8b
Notes and references
1 For reviews see: (a) S. D. Rychnovsky, Chem. Rev., 1995, 95,
2021–2040; (b) C. Schneider, Angew. Chem., Int. Ed., 1998, 37,
1375–1378; (c) S. E. Bode, M. Wolberg and M. Mu¨ller, Synthesis,
2006, 557–588; (d) R. D. Norcross and I. Paterson, Chem. Rev., 1995,
95, 2041–2114; (e) T. Oishi and T. Nakata, Synthesis, 1990, 635–645.
2 Selected examples: (a) M. Dieckmann and D. Menche, Org. Lett., 2013, 15,
228–231; (b) N. B. Kondekar and P. Kumar, Org. Lett., 2009, 11, 2611–2614;
(c) P. Walleser and R. Bru¨ckner, Eur. J. Org. Chem., 2010, 4802–4822;
(d) Z. Zhang, S. Aubry and Y. Kishi, Org. Lett., 2008, 10, 3077–3080.
3 (a) R. W. Hoffmann, Angew. Chem., Int. Ed., 2003, 42, 1096–1109;
(b) P. Kumar, P. S. Chowdhury and M. Pandey, Adv. Synth. Catal.,
2013, 355, 1719–1723; (c) T. Harada, T. Egusa, Y. Igarashi,
M. Kinugasa and A. Oku, J. Org. Chem., 2002, 67, 7080–7090;
9b
10c
11c
ˆ
(d) R. Chenevert and Y. S. Rose, J. Org. Chem., 2000, 65,
1707–1709; (e) C. Bonini, R. Racioppi, L. Viggiani, G. Righi and
L. Rossi, Tetrahedron: Asymmetry, 1993, 4, 793–805; ( f ) S. BouzBouz
and J. Cossy, Org. Lett., 2001, 3, 3995–3998.
4 (a) S. BouzBouz and J. Cossy, Org. Lett., 2000, 2, 501–504; (b) J. Cossy,
S. BouzBouz, F. Pradaux, C. Willis and V. Bellosta, Synlett, 2002,
1595–1606.
12c,d
5 (a) S. BouzBouz and J. Cossy, Org. Lett., 2000, 2, 3975–3977;
(b) S. BouzBouz and J. Cossy, Org. Lett., 2003, 5, 1995–1997;
(c) S. BouzBouz and J. Cossy, Tetrahedron Lett., 2003, 44, 4471–4473;
a
b
c
Overall isolated yields from 3 or 30. Conditions A. Conditions B.
´
(d) F. Allais and J. Cossy, Org. Lett., 2006, 8, 3655–3657; (e) L. Ferrie,
d
Reductive cleavage was performed using zinc in a THF–H2O mixture
L. Boulard, F. Pradaux, S. Bouzbouz, S. Reymond, P. Capdevielle and
J. Cossy, J. Org. Chem., 2008, 73, 1864–1880; ( f ) A. ElMarrouni,
A. Fukuda, M. Heras, S. Arseniyadis and J. Cossy, J. Org. Chem., 2010,
75, 8478–8486; (g) T. J. Hoffman, A. Kolleth, J. H. Rigby, S. Arseniyadis
and J. Cossy, Org. Lett., 2010, 12, 3348–3351; (h) J. Cossy, C. Willis,
V. Bellosta and L. Saint-Jalmes, Synthesis, 2002, 951–957.
6 See ESI‡ for the synthesis and characterization of 1a and 1b.
7 For reviews see: (a) S. J. Greco, R. G. Fiorot, V. J. Lacerda and R. Bezerra
dos Santos, Aldrichimica Acta, 2013, 46, 59–67; (b) C. Olier, M. Kaafarani,
S. Gastaldi and M. P. Bertrand, Tetrahedron, 2010, 66, 413–445;
(c) E. Arundale and L. A. Mikeska, Chem. Rev., 1952, 51, 505–555.
to prevent Boc migration.
the configuration of the homoallylic alcohol involved. In addi-
tion, as the unsaturated Boc-protected 1,3,5,7-tetraols can be
selectively functionalized, the use of these tetraols in the
synthesis of polyketide natural products is ongoing in our
laboratory and will be reported in due time.
6720 | Chem. Commun., 2014, 50, 6718--6721
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