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References
Castle, S. L.; McAtee, J. J. J. Am. Chem. Soc. 2000,
122, 7416–7417.
1. (a) Kazlauskas, R.; Lidgard, R. O.; Murphy, P. T.;
Wells, R. J. Tetrahedron Lett. 1980, 21, 2277–2280; (b)
Kazlauskas, R.; Lidgard, R. O.; Murphy, P. T.; Wells,
R. J.; Blount, J. F. Aust. J. Chem. 1981, 34, 765–786;
(c) Miao, S.; Andersen, R. J. J. Nat. Prod. 1990, 53,
1441–1446; (d) Pordesimo, E. O.; Schmitz, F. J. J. Org.
Chem. 1990, 55, 4704–4709; (e) Dexter, A. F.; Garson,
M. J.; Hemling, M. E. J. Nat. Prod. 1993, 56, 782–786;
(f) Gulavita, N. K.; Wright, A. E.; McCarthy, P. J.;
Pomponi, S. A.; Kelly-Borges, M.; Chin, M.; Sills, M.
A. J. Nat. Prod. 1993, 56, 1613–1617; (g) Jaspars, M.;
Rali, T.; Laney, M.; Schatzman, R. C.; Diaz, M. C.;
Schmitz, F. J.; Pordesimo, E. O.; Crews, P. Tetrahedron
1994, 50, 7367–7374; (h) Mack, M.; Molinski, T. F.;
Buck, E. D.; Pessah, I. N. J. Biol. Chem. 1994, 269,
23236–23349; (i) Park, S. K.; Jurek, J.; Carney, J. R.;
Scheuer, P. J. J. Nat. Prod. 1994, 57, 407–410; (j)
Franklin, M. A.; Penn, S. G.; Lebrilla, C. B.; Lam, T.
H.; Pessah, I. N.; Molinski, T. F. J. Nat. Prod. 1996,
59, 1121–1127.
11. Pschoor, R. Justus Liebigs Anal. Chem. 1912, 29.
12. Wymann, W. E.; Davis, R.; Patterson, J. W., Jr.;
Pfister, J. R. Synth. Commun. 1988, 18, 1379–1384.
13. Thomas, R. M.; Mohan, G. H.; Iyengar, D. S. Tetra-
hedron Lett. 1997, 38, 4721.
14. Phosphonate 14 was made in 79% from ethyl glyoxy-
late (two steps). For phosphonate preparation, see:
Nakamura, E. Tetrahedron Lett. 1981, 22, 663; for TBS
protection, see: Plantier-Royon, R.; Anker, D.; Robert-
Baudouy, J. J. Carbohydr. Chem. 1991, 10, 239.
15. The E-oxime configuration in 18 assigned by 13C NMR
which correlates with an upfield shift (l 30.9 ppm)
caused by steric compression of the a-CH2 carbon in
E-ketoximines, as seen in all bastadins (l ꢀ28–29 ppm,
see Ref. 1), compared to the corresponding signal in
Z-ketoximes (l ꢀ35 ppm), cf. Arabshahi, L.; Schmitz,
F. J. J. Org. Chem. 1987, 52, 3584.
16. (a) Corey, E. J.; Suggs, J. W. J. Org. Chem. 1973, 38,
3224; (b) Grieco, P. A.; Nishizawa, M.; Marinovic, N.;
Ehmann, W. J. Am. Chem. Soc. 1976, 98, 7102.
2. Coll, J. C.; Kearns, P. S.; Rideout, J. A.; Sankar, V. J.
Nat. Prod. 2002, 65, 753–756.
3. Carney, J. R.; Scheuer, P. J.; Kelly-Borges, M. J. Nat.
Prod. 1993, 56, 153–157.
17. Aldehyde 20 was prepared in 98% yield by nitration of
10, cf.: Michael, F. J.; Noffz, D. Chem. Ber. 1957, 90,
1586.
4. Pessah, I. N.; Molinski, T. F.; Meloy, T. D.; Wong, P.;
Buck, E. D.; Allen, P. D.; Mohr, F. C.; Mack, M. M.
Am. J. Physiol. 1997, 41, C601.
5. (a) Nishiyama, S.; Suzuki, T.; Yamamura, S. Chem.
Lett. 1982, 1851; (b) Nishiyama, S.; Yamamura, S. Tet-
rahedron Lett. 1982, 23, 1281.
18. Use of the meta-nitrobenzaldehyde 20, rather than the
ortho-nitro isomer, could provide analogs of 1 that
locate a photoaffinity label at a site removed from
steric congestion next to the diaryl ether bond. Model
studies (Bailey, K. B. Ph.D. thesis, 2002, University of
California, Davis) show that 3-bromo-4-fluorobenzalde-
hyde is sufficiently activated to participate in similar
SNAr displacements. Therefore, the meta-NO2 group in
20 imparts little or no activation, as expected.
6. Guo, Z. W.; Machiya, K.; Salamonczyk, G. M.; Sih, C.
J. J. Org. Chem. 1998, 63, 4269.
7. For
a discussion on regioisomers produced from
tandem macrolactamization of pairs of bis-azlactone-
diamines, see: Bailey, K. L.; Molinski, T. F. J. Org.
Chem. 1999, 64, 2501.
19. Corey, E. J.; Choi, S. Tetrahedron Lett. 1993, 34, 6969.
20. Pfp ester 24 (50.0 mg, 0.03 mmol) was stirred in
CH2Cl2 saturated with HCl(g) (2 mL) at pH 2 for 5 h.
Additional CH2Cl2 was added to a dilution of 0.005 M,
and reaction mixture adjusted to pH 8 with TEA. The
macrolactamization proceeded at ambient temperature
for 3 days. The mixture was concentrated and purified
over SiO2 to give 24 as a tan oil (21.3 mg, 60%); 1H
NMR (400 MHz, CDCl3) l 2.57 (t, J=6.0 Hz), 2.76 (t,
J=6.0 Hz, 2H), 3.28 (dd, J=6.0, 6.0 Hz, 2H), 3.49
(dd, J=6.0, 6.0 Hz, 2H), 3.80 (s, 3H), 3.87 (s, 2H),
3.95 (s, 3H), 4.11 (s, 2H), 5.11 (s, 2H), 5.16 (s, 2H),
6.43 (d, J=2.0 Hz, 1H), 6.59 (t, J=6.0 Hz, 1H), 6.81
(d, J=8.4 Hz, 1H), 6.85 (t, J=6.0 Hz, 1H), 6.95 (d,
J=2.0 Hz, 1H), 7.00 (s, 1H), 7.05 (dd, J=2.0, 8.4 Hz,
1H), 7.20 (dd, J=2.0, 8.4 Hz, 1H), 7.28 (m, 10H), 7.35
(d, J=8.4 Hz, 1H), 7.38 (d, J=8.4 Hz, 1H), 7.42 (dd,
J=2.0, 8.4 Hz, 1H), 7.56 (s, 1H); 13C NMR (100.5
MHz, CDCl3) l 26.7 (CH3), 28.7 (CH2), 34.8 (CH2),
34.9 (CH2), 40.2 (CH2), 40.7 (CH2), 61.1 (CH3), 61.3
(CH3), 77.6 (CH2), 77.7 (CH2), 112.2 (CH), 114.7 (C),
117.3 (CH), 117.5 (C), 118.0 (C), 118.3 (C), 118.8 (C),
120.8.5 (CH), 121.7 (CH), 128.2 (CH), 128.3 (CH),
128.5 (CH), 128.6 (CH), 128.7 (CH), 129.5 (CH), 131.4
(CH), 133.9 (C), 134.0 (CH), 135.8 (C), 136.2 (C), 136.5
(CH), 136.7 (C), 146.0 (C), 147.5 (C), 147.6 (C), 148.6
8. (a) Couladouros, E. A.; Moutsos, V. I. Tetrahedron
Lett. 1999, 7027; (b) Nicolaou, K. C.; Boddy, C. N. C.;
Natarajan, S.; Yue, T. Y.; Li, H.; Bra¨se, S.; Raman-
julu, J. M. J. Am. Chem. Soc. 1997, 119, 3421. For an
example of triazene meditated coupling applied to bas-
tadin-12, see: Couladouros, E. A.; Moutsos, V. I. Tet-
rahedron Lett. 1999, 40, 7023.
9. Leone-Stumpf, D.; Lindel, T. Chem. Eur. J. 2001, 7,
3961.
10. For recent examples of intramolecular SNAr ring clo-
sure in natural products synthesis, see: (a) Evans, D.
A.; Wood, M. R.; Watson, P. S.; Trotter, B. W.;
Richardson, T. I.; Barrow, J. C.; Katz, J. L. Angew.
Chem., Int. Ed. 1998, 37, 2700–2704; (b) Mori, Y.;
McAtee, J. J.; Rogel, O.; Boger, D. L. Tetrahedron
Lett. 2001, 42, 6061–6064; (c) Boger, D. L. Med. Res.
Rev. 2001, 21, 356–381; (c) Boger, D. L.; Kim, S. H.;
Mori, Y.; Weng, J. H.; Rogel, O.; Castle, S. L.; McA-
tee, J. J. J. Am. Chem. Soc. 2001, 123, 1862–1871; (d)
Boger, D. L.; Weng, J. H.; Miyazaki, S.; McAtee, J. J.;
Castle, S. L.; Kim, S. H.; Mori, Y.; Rogel, O.;
Strittmatter, H.; Jin, Q. J. Am. Chem. Soc. 2000, 122,
10047–10055; (e) Boger, D. L.; Kim, S. H.; Miyazaki,