A synthetic approach to diaryl ethers using the Robinson annulation

Tetrahedron Asymmetry

Volumn 10, Issue 1, 1999, Pages 99-105

  Feng, Xianqi ^a   Edstrom, Eric D ^a  

^a UNIVERSITY OF MONTANA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ETHER DERIVATIVE; GLUTAMIC ACID 5 METHYL ESTER; GLUTAMIC ACID DERIVATIVE; KETONE DERIVATIVE; N BENZYLOXYCARBONYL N,O ISOPROPYLIDENYL 3 PHENOXYTYROSINOL; OXAZOLIDINE DERIVATIVE; PHENOXYMETHYLVINYLKETONE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0033556608     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00466-2     Document Type: Article

References (34)

1. For recent reviews of synthetic efforts towards diaryl ether peptides, see: (a) Williams, R. M.; Hendrix, J. A. Chem. Rev. 1992, 92, 889-917. (b) Rao, A. V.; Gurjar, M. K.; Reddy, K. L.; Rao, A. S. Chem. Rev. 1995, 92, 2135-2167. Zhu, J. Synlett 1997, 133-144.
2. For recent reviews of synthetic efforts towards diaryl ether peptides, see: (a) Williams, R. M.; Hendrix, J. A. Chem. Rev. 1992, 92, 889-917. (b) Rao, A. V.; Gurjar, M. K.; Reddy, K. L.; Rao, A. S. Chem. Rev. 1995, 92, 2135-2167. Zhu, J. Synlett 1997, 133-144.
3. For recent reviews of synthetic efforts towards diaryl ether peptides, see: (a) Williams, R. M.; Hendrix, J. A. Chem. Rev. 1992, 92, 889-917. (b) Rao, A. V.; Gurjar, M. K.; Reddy, K. L.; Rao, A. S. Chem. Rev. 1995, 92, 2135-2167. Zhu, J. Synlett 1997, 133-144.
4. (a) Boger, D. L.; Yohannes, D. Tetrahedron Lett. 1989, 30, 2053-2056.
5. (b) Jung, M. E.; Jachiet, D.; Rohloff, J. C. Tetrahedron Lett. 1989, 30, 4211-4214.
6. (c) Jung, M. E.; Starkey, L. S. Tetrahedron 1997, 53, 8815-8824.
7. (a) Evans, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1989, 111, 1063-1072.
8. (b) Boger, D. L.; Yohannes, D. J. Org. Chem. 1990, 55, 6000-6017.
9. For the synthesis of deoxybouvardin and the pharmacophores of RA I-VII, see: (a) Boger, D. L.; Yohannes, D. J. Am. Chem. Soc. 1991, 113, 1427-1429. (b) Boger, D. L.; Myers Jr., J. B. J. Org. Chem. 1991, 56, 5385-5390. Boger, D. L.; Yohannes, D.; Myers Jr., J. B. J. Org. Chem. 1992, 57, 1319-1321. Boger, D. L.; Yohannes, D. J. Org. Chem. 1988, 53, 487-549. (e) Inaba, T.; Umezawa, I.; Yuasa, M.; Inoue, T.; Mihashi, S.; Itokawa, H.; Ogura K. J. Org. Chem. 1987, 52, 2957-2958. (f) Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544-8556. (g) Inoue, T.; Sasaki, T.; Takayanagi, H.; Harigaya, Y.; Hoshino, O.; Hara, H.; Inaba, T. J. Org. Chem. 1996, 61, 3936-3937. (h) Boger, D. L.; Zhou, J. J. Org. Chem. 1996, 61, 3938-3939. Boger, D. L.; Zhou, J.; Borzilleri; Nukui, S.; Castle, S. L. J. Org. Chem. 1997, 62, 2054-2069. (j) Beugelmans, R.; Bigot, A.; Bois-Choussy, M.; Zhu, J. J. Org. Chem. 1996, 61, 771-774. (k) Bigot, A; Beugelmans, R.; Zhu, J. Tetrahedron 1997, 53, 10753-10764. Bigot, A.; Zhu, J. Tetrahedron Lett. 1998, 39, 551-554. For structures and antitumor activities of RA derivatives (bouvardin), see: Itokawa, H.; Kondo, K.; Hitotsuyanagi, Y.; Nakamura, A.; Morita, H.; Takeya, K. Chem. Pharm. Bull. 1993, 41, 1266-1269.
10. For the synthesis of deoxybouvardin and the pharmacophores of RA I-VII, see: (a) Boger, D. L.; Yohannes, D. J. Am. Chem. Soc. 1991, 113, 1427-1429. (b) Boger, D. L.; Myers Jr., J. B. J. Org. Chem. 1991, 56, 5385-5390. Boger, D. L.; Yohannes, D.; Myers Jr., J. B. J. Org. Chem. 1992, 57, 1319-1321. Boger, D. L.; Yohannes, D. J. Org. Chem. 1988, 53, 487-549. (e) Inaba, T.; Umezawa, I.; Yuasa, M.; Inoue, T.; Mihashi, S.; Itokawa, H.; Ogura K. J. Org. Chem. 1987, 52, 2957-2958. (f) Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544-8556. (g) Inoue, T.; Sasaki, T.; Takayanagi, H.; Harigaya, Y.; Hoshino, O.; Hara, H.; Inaba, T. J. Org. Chem. 1996, 61, 3936-3937. (h) Boger, D. L.; Zhou, J. J. Org. Chem. 1996, 61, 3938-3939. Boger, D. L.; Zhou, J.; Borzilleri; Nukui, S.; Castle, S. L. J. Org. Chem. 1997, 62, 2054-2069. (j) Beugelmans, R.; Bigot, A.; Bois-Choussy, M.; Zhu, J. J. Org. Chem. 1996, 61, 771-774. (k) Bigot, A; Beugelmans, R.; Zhu, J. Tetrahedron 1997, 53, 10753-10764. Bigot, A.; Zhu, J. Tetrahedron Lett. 1998, 39, 551-554. For structures and antitumor activities of RA derivatives (bouvardin), see: Itokawa, H.; Kondo, K.; Hitotsuyanagi, Y.; Nakamura, A.; Morita, H.; Takeya, K. Chem. Pharm. Bull. 1993, 41, 1266-1269.
11. For the synthesis of deoxybouvardin and the pharmacophores of RA I-VII, see: (a) Boger, D. L.; Yohannes, D. J. Am. Chem. Soc. 1991, 113, 1427-1429. (b) Boger, D. L.; Myers Jr., J. B. J. Org. Chem. 1991, 56, 5385-5390. Boger, D. L.; Yohannes, D.; Myers Jr., J. B. J. Org. Chem. 1992, 57, 1319-1321. Boger, D. L.; Yohannes, D. J. Org. Chem. 1988, 53, 487-549. (e) Inaba, T.; Umezawa, I.; Yuasa, M.; Inoue, T.; Mihashi, S.; Itokawa, H.; Ogura K. J. Org. Chem. 1987, 52, 2957-2958. (f) Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544-8556. (g) Inoue, T.; Sasaki, T.; Takayanagi, H.; Harigaya, Y.; Hoshino, O.; Hara, H.; Inaba, T. J. Org. Chem. 1996, 61, 3936-3937. (h) Boger, D. L.; Zhou, J. J. Org. Chem. 1996, 61, 3938-3939. Boger, D. L.; Zhou, J.; Borzilleri; Nukui, S.; Castle, S. L. J. Org. Chem. 1997, 62, 2054-2069. (j) Beugelmans, R.; Bigot, A.; Bois-Choussy, M.; Zhu, J. J. Org. Chem. 1996, 61, 771-774. (k) Bigot, A; Beugelmans, R.; Zhu, J. Tetrahedron 1997, 53, 10753-10764. Bigot, A.; Zhu, J. Tetrahedron Lett. 1998, 39, 551-554. For structures and antitumor activities of RA derivatives (bouvardin), see: Itokawa, H.; Kondo, K.; Hitotsuyanagi, Y.; Nakamura, A.; Morita, H.; Takeya, K. Chem. Pharm. Bull. 1993, 41, 1266-1269.
12. For the synthesis of deoxybouvardin and the pharmacophores of RA I-VII, see: (a) Boger, D. L.; Yohannes, D. J. Am. Chem. Soc. 1991, 113, 1427-1429. (b) Boger, D. L.; Myers Jr., J. B. J. Org. Chem. 1991, 56, 5385-5390. Boger, D. L.; Yohannes, D.; Myers Jr., J. B. J. Org. Chem. 1992, 57, 1319-1321. Boger, D. L.; Yohannes, D. J. Org. Chem. 1988, 53, 487-549. (e) Inaba, T.; Umezawa, I.; Yuasa, M.; Inoue, T.; Mihashi, S.; Itokawa, H.; Ogura K. J. Org. Chem. 1987, 52, 2957-2958. (f) Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544-8556. (g) Inoue, T.; Sasaki, T.; Takayanagi, H.; Harigaya, Y.; Hoshino, O.; Hara, H.; Inaba, T. J. Org. Chem. 1996, 61, 3936-3937. (h) Boger, D. L.; Zhou, J. J. Org. Chem. 1996, 61, 3938-3939. Boger, D. L.; Zhou, J.; Borzilleri; Nukui, S.; Castle, S. L. J. Org. Chem. 1997, 62, 2054-2069. (j) Beugelmans, R.; Bigot, A.; Bois-Choussy, M.; Zhu, J. J. Org. Chem. 1996, 61, 771-774. (k) Bigot, A; Beugelmans, R.; Zhu, J. Tetrahedron 1997, 53, 10753-10764. Bigot, A.; Zhu, J. Tetrahedron Lett. 1998, 39, 551-554. For structures and antitumor activities of RA derivatives (bouvardin), see: Itokawa, H.; Kondo, K.; Hitotsuyanagi, Y.; Nakamura, A.; Morita, H.; Takeya, K. Chem. Pharm. Bull. 1993, 41, 1266-1269.
13. For the synthesis of deoxybouvardin and the pharmacophores of RA I-VII, see: (a) Boger, D. L.; Yohannes, D. J. Am. Chem. Soc. 1991, 113, 1427-1429. (b) Boger, D. L.; Myers Jr., J. B. J. Org. Chem. 1991, 56, 5385-5390. Boger, D. L.; Yohannes, D.; Myers Jr., J. B. J. Org. Chem. 1992, 57, 1319-1321. Boger, D. L.; Yohannes, D. J. Org. Chem. 1988, 53, 487-549. (e) Inaba, T.; Umezawa, I.; Yuasa, M.; Inoue, T.; Mihashi, S.; Itokawa, H.; Ogura K. J. Org. Chem. 1987, 52, 2957-2958. (f) Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544-8556. (g) Inoue, T.; Sasaki, T.; Takayanagi, H.; Harigaya, Y.; Hoshino, O.; Hara, H.; Inaba, T. J. Org. Chem. 1996, 61, 3936-3937. (h) Boger, D. L.; Zhou, J. J. Org. Chem. 1996, 61, 3938-3939. Boger, D. L.; Zhou, J.; Borzilleri; Nukui, S.; Castle, S. L. J. Org. Chem. 1997, 62, 2054-2069. (j) Beugelmans, R.; Bigot, A.; Bois-Choussy, M.; Zhu, J. J. Org. Chem. 1996, 61, 771-774. (k) Bigot, A; Beugelmans, R.; Zhu, J. Tetrahedron 1997, 53, 10753-10764. Bigot, A.; Zhu, J. Tetrahedron Lett. 1998, 39, 551-554. For structures and antitumor activities of RA derivatives (bouvardin), see: Itokawa, H.; Kondo, K.; Hitotsuyanagi, Y.; Nakamura, A.; Morita, H.; Takeya, K. Chem. Pharm. Bull. 1993, 41, 1266-1269.
14. For the synthesis of deoxybouvardin and the pharmacophores of RA I-VII, see: (a) Boger, D. L.; Yohannes, D. J. Am. Chem. Soc. 1991, 113, 1427-1429. (b) Boger, D. L.; Myers Jr., J. B. J. Org. Chem. 1991, 56, 5385-5390. Boger, D. L.; Yohannes, D.; Myers Jr., J. B. J. Org. Chem. 1992, 57, 1319-1321. Boger, D. L.; Yohannes, D. J. Org. Chem. 1988, 53, 487-549. (e) Inaba, T.; Umezawa, I.; Yuasa, M.; Inoue, T.; Mihashi, S.; Itokawa, H.; Ogura K. J. Org. Chem. 1987, 52, 2957-2958. (f) Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544-8556. (g) Inoue, T.; Sasaki, T.; Takayanagi, H.; Harigaya, Y.; Hoshino, O.; Hara, H.; Inaba, T. J. Org. Chem. 1996, 61, 3936-3937. (h) Boger, D. L.; Zhou, J. J. Org. Chem. 1996, 61, 3938-3939. Boger, D. L.; Zhou, J.; Borzilleri; Nukui, S.; Castle, S. L. J. Org. Chem. 1997, 62, 2054-2069. (j) Beugelmans, R.; Bigot, A.; Bois-Choussy, M.; Zhu, J. J. Org. Chem. 1996, 61, 771-774. (k) Bigot, A; Beugelmans, R.; Zhu, J. Tetrahedron 1997, 53, 10753-10764. Bigot, A.; Zhu, J. Tetrahedron Lett. 1998, 39, 551-554. For structures and antitumor activities of RA derivatives (bouvardin), see: Itokawa, H.; Kondo, K.; Hitotsuyanagi, Y.; Nakamura, A.; Morita, H.; Takeya, K. Chem. Pharm. Bull. 1993, 41, 1266-1269.
15. For the synthesis of deoxybouvardin and the pharmacophores of RA I-VII, see: (a) Boger, D. L.; Yohannes, D. J. Am. Chem. Soc. 1991, 113, 1427-1429. (b) Boger, D. L.; Myers Jr., J. B. J. Org. Chem. 1991, 56, 5385-5390. Boger, D. L.; Yohannes, D.; Myers Jr., J. B. J. Org. Chem. 1992, 57, 1319-1321. Boger, D. L.; Yohannes, D. J. Org. Chem. 1988, 53, 487-549. (e) Inaba, T.; Umezawa, I.; Yuasa, M.; Inoue, T.; Mihashi, S.; Itokawa, H.; Ogura K. J. Org. Chem. 1987, 52, 2957-2958. (f) Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544-8556. (g) Inoue, T.; Sasaki, T.; Takayanagi, H.; Harigaya, Y.; Hoshino, O.; Hara, H.; Inaba, T. J. Org. Chem. 1996, 61, 3936-3937. (h) Boger, D. L.; Zhou, J. J. Org. Chem. 1996, 61, 3938-3939. Boger, D. L.; Zhou, J.; Borzilleri; Nukui, S.; Castle, S. L. J. Org. Chem. 1997, 62, 2054-2069. (j) Beugelmans, R.; Bigot, A.; Bois-Choussy, M.; Zhu, J. J. Org. Chem. 1996, 61, 771-774. (k) Bigot, A; Beugelmans, R.; Zhu, J. Tetrahedron 1997, 53, 10753-10764. Bigot, A.; Zhu, J. Tetrahedron Lett. 1998, 39, 551-554. For structures and antitumor activities of RA derivatives (bouvardin), see: Itokawa, H.; Kondo, K.; Hitotsuyanagi, Y.; Nakamura, A.; Morita, H.; Takeya, K. Chem. Pharm. Bull. 1993, 41, 1266-1269.
16. For the synthesis of deoxybouvardin and the pharmacophores of RA I-VII, see: (a) Boger, D. L.; Yohannes, D. J. Am. Chem. Soc. 1991, 113, 1427-1429. (b) Boger, D. L.; Myers Jr., J. B. J. Org. Chem. 1991, 56, 5385-5390. Boger, D. L.; Yohannes, D.; Myers Jr., J. B. J. Org. Chem. 1992, 57, 1319-1321. Boger, D. L.; Yohannes, D. J. Org. Chem. 1988, 53, 487-549. (e) Inaba, T.; Umezawa, I.; Yuasa, M.; Inoue, T.; Mihashi, S.; Itokawa, H.; Ogura K. J. Org. Chem. 1987, 52, 2957-2958. (f) Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544-8556. (g) Inoue, T.; Sasaki, T.; Takayanagi, H.; Harigaya, Y.; Hoshino, O.; Hara, H.; Inaba, T. J. Org. Chem. 1996, 61, 3936-3937. (h) Boger, D. L.; Zhou, J. J. Org. Chem. 1996, 61, 3938-3939. Boger, D. L.; Zhou, J.; Borzilleri; Nukui, S.; Castle, S. L. J. Org. Chem. 1997, 62, 2054-2069. (j) Beugelmans, R.; Bigot, A.; Bois-Choussy, M.; Zhu, J. J. Org. Chem. 1996, 61, 771-774. (k) Bigot, A; Beugelmans, R.; Zhu, J. Tetrahedron 1997, 53, 10753-10764. Bigot, A.; Zhu, J. Tetrahedron Lett. 1998, 39, 551-554. For structures and antitumor activities of RA derivatives (bouvardin), see: Itokawa, H.; Kondo, K.; Hitotsuyanagi, Y.; Nakamura, A.; Morita, H.; Takeya, K. Chem. Pharm. Bull. 1993, 41, 1266-1269.
17. For the synthesis of deoxybouvardin and the pharmacophores of RA I-VII, see: (a) Boger, D. L.; Yohannes, D. J. Am. Chem. Soc. 1991, 113, 1427-1429. (b) Boger, D. L.; Myers Jr., J. B. J. Org. Chem. 1991, 56, 5385-5390. Boger, D. L.; Yohannes, D.; Myers Jr., J. B. J. Org. Chem. 1992, 57, 1319-1321. Boger, D. L.; Yohannes, D. J. Org. Chem. 1988, 53, 487-549. (e) Inaba, T.; Umezawa, I.; Yuasa, M.; Inoue, T.; Mihashi, S.; Itokawa, H.; Ogura K. J. Org. Chem. 1987, 52, 2957-2958. (f) Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544-8556. (g) Inoue, T.; Sasaki, T.; Takayanagi, H.; Harigaya, Y.; Hoshino, O.; Hara, H.; Inaba, T. J. Org. Chem. 1996, 61, 3936-3937. (h) Boger, D. L.; Zhou, J. J. Org. Chem. 1996, 61, 3938-3939. Boger, D. L.; Zhou, J.; Borzilleri; Nukui, S.; Castle, S. L. J. Org. Chem. 1997, 62, 2054-2069. (j) Beugelmans, R.; Bigot, A.; Bois-Choussy, M.; Zhu, J. J. Org. Chem. 1996, 61, 771-774. (k) Bigot, A; Beugelmans, R.; Zhu, J. Tetrahedron 1997, 53, 10753-10764. Bigot, A.; Zhu, J. Tetrahedron Lett. 1998, 39, 551-554. For structures and antitumor activities of RA derivatives (bouvardin), see: Itokawa, H.; Kondo, K.; Hitotsuyanagi, Y.; Nakamura, A.; Morita, H.; Takeya, K. Chem. Pharm. Bull. 1993, 41, 1266-1269.
18. For the synthesis of deoxybouvardin and the pharmacophores of RA I-VII, see: (a) Boger, D. L.; Yohannes, D. J. Am. Chem. Soc. 1991, 113, 1427-1429. (b) Boger, D. L.; Myers Jr., J. B. J. Org. Chem. 1991, 56, 5385-5390. Boger, D. L.; Yohannes, D.; Myers Jr., J. B. J. Org. Chem. 1992, 57, 1319-1321. Boger, D. L.; Yohannes, D. J. Org. Chem. 1988, 53, 487-549. (e) Inaba, T.; Umezawa, I.; Yuasa, M.; Inoue, T.; Mihashi, S.; Itokawa, H.; Ogura K. J. Org. Chem. 1987, 52, 2957-2958. (f) Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544-8556. (g) Inoue, T.; Sasaki, T.; Takayanagi, H.; Harigaya, Y.; Hoshino, O.; Hara, H.; Inaba, T. J. Org. Chem. 1996, 61, 3936-3937. (h) Boger, D. L.; Zhou, J. J. Org. Chem. 1996, 61, 3938-3939. Boger, D. L.; Zhou, J.; Borzilleri; Nukui, S.; Castle, S. L. J. Org. Chem. 1997, 62, 2054-2069. (j) Beugelmans, R.; Bigot, A.; Bois-Choussy, M.; Zhu, J. J. Org. Chem. 1996, 61, 771-774. (k) Bigot, A; Beugelmans, R.; Zhu, J. Tetrahedron 1997, 53, 10753-10764. Bigot, A.; Zhu, J. Tetrahedron Lett. 1998, 39, 551-554. For structures and antitumor activities of RA derivatives (bouvardin), see: Itokawa, H.; Kondo, K.; Hitotsuyanagi, Y.; Nakamura, A.; Morita, H.; Takeya, K. Chem. Pharm. Bull. 1993, 41, 1266-1269.
19. For the synthesis of deoxybouvardin and the pharmacophores of RA I-VII, see: (a) Boger, D. L.; Yohannes, D. J. Am. Chem. Soc. 1991, 113, 1427-1429. (b) Boger, D. L.; Myers Jr., J. B. J. Org. Chem. 1991, 56, 5385-5390. Boger, D. L.; Yohannes, D.; Myers Jr., J. B. J. Org. Chem. 1992, 57, 1319-1321. Boger, D. L.; Yohannes, D. J. Org. Chem. 1988, 53, 487-549. (e) Inaba, T.; Umezawa, I.; Yuasa, M.; Inoue, T.; Mihashi, S.; Itokawa, H.; Ogura K. J. Org. Chem. 1987, 52, 2957-2958. (f) Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544-8556. (g) Inoue, T.; Sasaki, T.; Takayanagi, H.; Harigaya, Y.; Hoshino, O.; Hara, H.; Inaba, T. J. Org. Chem. 1996, 61, 3936-3937. (h) Boger, D. L.; Zhou, J. J. Org. Chem. 1996, 61, 3938-3939. Boger, D. L.; Zhou, J.; Borzilleri; Nukui, S.; Castle, S. L. J. Org. Chem. 1997, 62, 2054-2069. (j) Beugelmans, R.; Bigot, A.; Bois-Choussy, M.; Zhu, J. J. Org. Chem. 1996, 61, 771-774. (k) Bigot, A; Beugelmans, R.; Zhu, J. Tetrahedron 1997, 53, 10753-10764. Bigot, A.; Zhu, J. Tetrahedron Lett. 1998, 39, 551-554. For structures and antitumor activities of RA derivatives (bouvardin), see: Itokawa, H.; Kondo, K.; Hitotsuyanagi, Y.; Nakamura, A.; Morita, H.; Takeya, K. Chem. Pharm. Bull. 1993, 41, 1266-1269.
20. For the synthesis of deoxybouvardin and the pharmacophores of RA I-VII, see: (a) Boger, D. L.; Yohannes, D. J. Am. Chem. Soc. 1991, 113, 1427-1429. (b) Boger, D. L.; Myers Jr., J. B. J. Org. Chem. 1991, 56, 5385-5390. Boger, D. L.; Yohannes, D.; Myers Jr., J. B. J. Org. Chem. 1992, 57, 1319-1321. Boger, D. L.; Yohannes, D. J. Org. Chem. 1988, 53, 487-549. (e) Inaba, T.; Umezawa, I.; Yuasa, M.; Inoue, T.; Mihashi, S.; Itokawa, H.; Ogura K. J. Org. Chem. 1987, 52, 2957-2958. (f) Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544-8556. (g) Inoue, T.; Sasaki, T.; Takayanagi, H.; Harigaya, Y.; Hoshino, O.; Hara, H.; Inaba, T. J. Org. Chem. 1996, 61, 3936-3937. (h) Boger, D. L.; Zhou, J. J. Org. Chem. 1996, 61, 3938-3939. Boger, D. L.; Zhou, J.; Borzilleri; Nukui, S.; Castle, S. L. J. Org. Chem. 1997, 62, 2054-2069. (j) Beugelmans, R.; Bigot, A.; Bois-Choussy, M.; Zhu, J. J. Org. Chem. 1996, 61, 771-774. (k) Bigot, A; Beugelmans, R.; Zhu, J. Tetrahedron 1997, 53, 10753-10764. Bigot, A.; Zhu, J. Tetrahedron Lett. 1998, 39, 551-554. For structures and antitumor activities of RA derivatives (bouvardin), see: Itokawa, H.; Kondo, K.; Hitotsuyanagi, Y.; Nakamura, A.; Morita, H.; Takeya, K. Chem. Pharm. Bull. 1993, 41, 1266-1269.
21. For the synthesis of deoxybouvardin and the pharmacophores of RA I-VII, see: (a) Boger, D. L.; Yohannes, D. J. Am. Chem. Soc. 1991, 113, 1427-1429. (b) Boger, D. L.; Myers Jr., J. B. J. Org. Chem. 1991, 56, 5385-5390. Boger, D. L.; Yohannes, D.; Myers Jr., J. B. J. Org. Chem. 1992, 57, 1319-1321. Boger, D. L.; Yohannes, D. J. Org. Chem. 1988, 53, 487-549. (e) Inaba, T.; Umezawa, I.; Yuasa, M.; Inoue, T.; Mihashi, S.; Itokawa, H.; Ogura K. J. Org. Chem. 1987, 52, 2957-2958. (f) Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544-8556. (g) Inoue, T.; Sasaki, T.; Takayanagi, H.; Harigaya, Y.; Hoshino, O.; Hara, H.; Inaba, T. J. Org. Chem. 1996, 61, 3936-3937. (h) Boger, D. L.; Zhou, J. J. Org. Chem. 1996, 61, 3938-3939. Boger, D. L.; Zhou, J.; Borzilleri; Nukui, S.; Castle, S. L. J. Org. Chem. 1997, 62, 2054-2069. (j) Beugelmans, R.; Bigot, A.; Bois-Choussy, M.; Zhu, J. J. Org. Chem. 1996, 61, 771-774. (k) Bigot, A; Beugelmans, R.; Zhu, J. Tetrahedron 1997, 53, 10753-10764. Bigot, A.; Zhu, J. Tetrahedron Lett. 1998, 39, 551-554. For structures and antitumor activities of RA derivatives (bouvardin), see: Itokawa, H.; Kondo, K.; Hitotsuyanagi, Y.; Nakamura, A.; Morita, H.; Takeya, K. Chem. Pharm. Bull. 1993, 41, 1266-1269.
22. Evans, D. A.; Barrow, J. C.; Watson, P. S.; Ratz, A. M.; Dinsmore, C. J.; Evrard, D. A.; Devries, K. M.; Ellman, J. A.; Rychnovsky, S. D.; Lacour, J. J. Am. Chem. Soc. 1997, 119, 3419-3420.
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31. For aromatization procedures, see: (a) Bondon, D.; Pietrasanta, Y.; Pucci, B. Tetrahedron Lett. 1977, 821-882. (b) Hirao, T.; Mori, M.; Ohshiro, Y. J. Org. Chem. 1990, 55, 358-360. Paquette, L. A.; Thompson, R. C. J. Org. Chem. 1993, 58, 4952-4962. Sharpless, K. B.; Lauer, R. F.; Teranishi, A. Y. J. Am. Chem. Soc. 1973, 95, 6137.
32. For aromatization procedures, see: (a) Bondon, D.; Pietrasanta, Y.; Pucci, B. Tetrahedron Lett. 1977, 821-882. (b) Hirao, T.; Mori, M.; Ohshiro, Y. J. Org. Chem. 1990, 55, 358-360. Paquette, L. A.; Thompson, R. C. J. Org. Chem. 1993, 58, 4952-4962. Sharpless, K. B.; Lauer, R. F.; Teranishi, A. Y. J. Am. Chem. Soc. 1973, 95, 6137.
33. For aromatization procedures, see: (a) Bondon, D.; Pietrasanta, Y.; Pucci, B. Tetrahedron Lett. 1977, 821-882. (b) Hirao, T.; Mori, M.; Ohshiro, Y. J. Org. Chem. 1990, 55, 358-360. Paquette, L. A.; Thompson, R. C. J. Org. Chem. 1993, 58, 4952-4962. Sharpless, K. B.; Lauer, R. F.; Teranishi, A. Y. J. Am. Chem. Soc. 1973, 95, 6137.
34. For aromatization procedures, see: (a) Bondon, D.; Pietrasanta, Y.; Pucci, B. Tetrahedron Lett. 1977, 821-882. (b) Hirao, T.; Mori, M.; Ohshiro, Y. J. Org. Chem. 1990, 55, 358-360. Paquette, L. A.; Thompson, R. C. J. Org. Chem. 1993, 58, 4952-4962. Sharpless, K. B.; Lauer, R. F.; Teranishi, A. Y. J. Am. Chem. Soc. 1973, 95, 6137.