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Scheme 3. Reagents and conditions: (a) TBAF, THF, 25°C, 1
h, 98%; (b) CAN, MeCN–H2O (4:1), 0°C, 10 min, 85%; (c)
Pd/C, H2, MeOH, 96%; (d) TFA–CH2Cl2 1:1, 0°C, 20 min,
85%.
the regioselective AA reaction of 1, the present strategy
represents a general solution for the complete asymmet-
ric synthesis of ABTs from the readily available achiral
olefin 1.15 Total asymmetric synthesis of the molecules
in Figure 1, which is employing the orthogonally pro-
tected ABTs as key synthetic intermediates, is currently
underway, and will be reported in due course.
4. Marino, P.; Franco, S.; Merchan, F. L.; Revuelta, J.;
Tejero, T. Tetrahedron Lett. 2002, 43, 459.
5. Fadnavis, N. W.; Sharfuddin, M.; Vadivel, S. K. Tetra-
hedron: Asymmetry 2001, 12, 691.
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7. (a) Han, H.; Cho, C. W.; Janda, K. D. Chem. Eur. J.
1999, 5, 1565. For other similar approaches, see: (b)
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Acknowledgements
Financial support from National Institute of Health
(GM 08194) and The Welch Foundation (AX-1534) is
gratefully acknowledged.
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