Variable strategy toward carbasugars and relatives. 5. Focus on preparation of chiral nonracemic medium-sized carbocycles

Journal of Organic Chemistry

Volumn 68, Issue 15, 2003, Pages 5881-5885

  Rassu, Gloria ^a   Auzzas, Luciana ^a   Pinna, Luigi ^b   Zambrano, Vincenzo ^b   Zanardi, Franca ^c   Battistini, Lucia ^c   Gaetani, Enrico ^c   Curti, Claudio ^c   Casiraghi, Giovanni ^c  

^a CNR   (Italy)

^b UNIVERSITY OF SASSARI   (Italy)

^c UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CARBOHYDRATES; SUBSTITUTION REACTIONS;

LEWIS ACIDS;

FURAN RESINS;

ALCOHOL; ALDEHYDE; CARBAOCTANOSE; CARBASEPTANOSE; CARBASUGAR; CARBOCYCLE DERIVATIVE; CARBOHYDRATE; CYCLOHEXANE; CYCLOPENTANE; DIHYDRO 5H FURAN 2 ONE ALDEHYDE; FURAN DERIVATIVE; HEPTOSE; LEWIS ACID; MACROCYCLIC COMPOUND; PYRROLE DERIVATIVE; PYRROLIDIN 2 ONE ALDEHYDE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ALDOL REACTION; ARTICLE; CHIRALITY; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037700759     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0344539     Document Type: Article

References (53)

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15. For selected references on the synthesis of carbaseptanose and carbaoctanose derivatives, see: (a) Wang, W.; Zhang, Y.; Sollogoub, M.; Sinaÿ, P. Angew. Chem., Int. Ed. 2000, 39, 2466-2467. (b) Wang, W.; Zhang, Y.; Zhou, H.; Blériot, Y.; Sinaÿ, P. Eur. J. Org. Chem. 2001, 1053-1059. (c) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2002, 67, 3705-3717. (d) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2000, 65, 5416-5419. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651-2654. (f) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094-4096. (g) van Hooft, P. A. V.; Litjens, R. E. J. N.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Org. Lett. 2001, 3, 731-733. (h) McNulty, J.; Grunner, V.; Mao, J. Tetrahedron Lett. 2001, 42, 5609-5612. (i) Pearson, A. J.; Katiyar, S. Tetrahedron 2000, 56, 2297-2304. (j) Roy, A.; Chakrabarty, K.; Dutta, P. K.; Bar, N. C.; Basu, N.; Achari, B.; Mandal, S. B. J. Org. Chem. 1999, 64, 2304-2309. (k) Patra, R.; Bar, N. C.; Roy, A.; Achari, B.; Ghoshal, N.; Mandal, S. B. Tetrahedron 1996, 52, 11265-11272. (l) Le Merrer, Y.; Gravier-Pelletier, C.; Maton, W.; Numa, M.; Depezay, J.-C. Synlett 1999, 1322-1324. (m) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475-4478. (n) Blériot, Y.; Giroult, A.; Mallet, J.-M.; Rodriguez, E.; Vogel, P.; Sinaÿ, P. Tetrahedron: Asymmetry 2002, 13, 2553-2565.
16. For selected references on the synthesis of carbaseptanose and carbaoctanose derivatives, see: (a) Wang, W.; Zhang, Y.; Sollogoub, M.; Sinaÿ, P. Angew. Chem., Int. Ed. 2000, 39, 2466-2467. (b) Wang, W.; Zhang, Y.; Zhou, H.; Blériot, Y.; Sinaÿ, P. Eur. J. Org. Chem. 2001, 1053-1059. (c) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2002, 67, 3705-3717. (d) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2000, 65, 5416-5419. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651-2654. (f) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094-4096. (g) van Hooft, P. A. V.; Litjens, R. E. J. N.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Org. Lett. 2001, 3, 731-733. (h) McNulty, J.; Grunner, V.; Mao, J. Tetrahedron Lett. 2001, 42, 5609-5612. (i) Pearson, A. J.; Katiyar, S. Tetrahedron 2000, 56, 2297-2304. (j) Roy, A.; Chakrabarty, K.; Dutta, P. K.; Bar, N. C.; Basu, N.; Achari, B.; Mandal, S. B. J. Org. Chem. 1999, 64, 2304-2309. (k) Patra, R.; Bar, N. C.; Roy, A.; Achari, B.; Ghoshal, N.; Mandal, S. B. Tetrahedron 1996, 52, 11265-11272. (l) Le Merrer, Y.; Gravier-Pelletier, C.; Maton, W.; Numa, M.; Depezay, J.-C. Synlett 1999, 1322-1324. (m) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475-4478. (n) Blériot, Y.; Giroult, A.; Mallet, J.-M.; Rodriguez, E.; Vogel, P.; Sinaÿ, P. Tetrahedron: Asymmetry 2002, 13, 2553-2565.
17. For selected references on the synthesis of carbaseptanose and carbaoctanose derivatives, see: (a) Wang, W.; Zhang, Y.; Sollogoub, M.; Sinaÿ, P. Angew. Chem., Int. Ed. 2000, 39, 2466-2467. (b) Wang, W.; Zhang, Y.; Zhou, H.; Blériot, Y.; Sinaÿ, P. Eur. J. Org. Chem. 2001, 1053-1059. (c) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2002, 67, 3705-3717. (d) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2000, 65, 5416-5419. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651-2654. (f) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094-4096. (g) van Hooft, P. A. V.; Litjens, R. E. J. N.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Org. Lett. 2001, 3, 731-733. (h) McNulty, J.; Grunner, V.; Mao, J. Tetrahedron Lett. 2001, 42, 5609-5612. (i) Pearson, A. J.; Katiyar, S. Tetrahedron 2000, 56, 2297-2304. (j) Roy, A.; Chakrabarty, K.; Dutta, P. K.; Bar, N. C.; Basu, N.; Achari, B.; Mandal, S. B. J. Org. Chem. 1999, 64, 2304-2309. (k) Patra, R.; Bar, N. C.; Roy, A.; Achari, B.; Ghoshal, N.; Mandal, S. B. Tetrahedron 1996, 52, 11265-11272. (l) Le Merrer, Y.; Gravier-Pelletier, C.; Maton, W.; Numa, M.; Depezay, J.-C. Synlett 1999, 1322-1324. (m) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475-4478. (n) Blériot, Y.; Giroult, A.; Mallet, J.-M.; Rodriguez, E.; Vogel, P.; Sinaÿ, P. Tetrahedron: Asymmetry 2002, 13, 2553-2565.
18. For selected references on the synthesis of carbaseptanose and carbaoctanose derivatives, see: (a) Wang, W.; Zhang, Y.; Sollogoub, M.; Sinaÿ, P. Angew. Chem., Int. Ed. 2000, 39, 2466-2467. (b) Wang, W.; Zhang, Y.; Zhou, H.; Blériot, Y.; Sinaÿ, P. Eur. J. Org. Chem. 2001, 1053-1059. (c) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2002, 67, 3705-3717. (d) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2000, 65, 5416-5419. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651-2654. (f) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094-4096. (g) van Hooft, P. A. V.; Litjens, R. E. J. N.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Org. Lett. 2001, 3, 731-733. (h) McNulty, J.; Grunner, V.; Mao, J. Tetrahedron Lett. 2001, 42, 5609-5612. (i) Pearson, A. J.; Katiyar, S. Tetrahedron 2000, 56, 2297-2304. (j) Roy, A.; Chakrabarty, K.; Dutta, P. K.; Bar, N. C.; Basu, N.; Achari, B.; Mandal, S. B. J. Org. Chem. 1999, 64, 2304-2309. (k) Patra, R.; Bar, N. C.; Roy, A.; Achari, B.; Ghoshal, N.; Mandal, S. B. Tetrahedron 1996, 52, 11265-11272. (l) Le Merrer, Y.; Gravier-Pelletier, C.; Maton, W.; Numa, M.; Depezay, J.-C. Synlett 1999, 1322-1324. (m) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475-4478. (n) Blériot, Y.; Giroult, A.; Mallet, J.-M.; Rodriguez, E.; Vogel, P.; Sinaÿ, P. Tetrahedron: Asymmetry 2002, 13, 2553-2565.
19. For selected references on the synthesis of carbaseptanose and carbaoctanose derivatives, see: (a) Wang, W.; Zhang, Y.; Sollogoub, M.; Sinaÿ, P. Angew. Chem., Int. Ed. 2000, 39, 2466-2467. (b) Wang, W.; Zhang, Y.; Zhou, H.; Blériot, Y.; Sinaÿ, P. Eur. J. Org. Chem. 2001, 1053-1059. (c) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2002, 67, 3705-3717. (d) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2000, 65, 5416-5419. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651-2654. (f) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094-4096. (g) van Hooft, P. A. V.; Litjens, R. E. J. N.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Org. Lett. 2001, 3, 731-733. (h) McNulty, J.; Grunner, V.; Mao, J. Tetrahedron Lett. 2001, 42, 5609-5612. (i) Pearson, A. J.; Katiyar, S. Tetrahedron 2000, 56, 2297-2304. (j) Roy, A.; Chakrabarty, K.; Dutta, P. K.; Bar, N. C.; Basu, N.; Achari, B.; Mandal, S. B. J. Org. Chem. 1999, 64, 2304-2309. (k) Patra, R.; Bar, N. C.; Roy, A.; Achari, B.; Ghoshal, N.; Mandal, S. B. Tetrahedron 1996, 52, 11265-11272. (l) Le Merrer, Y.; Gravier-Pelletier, C.; Maton, W.; Numa, M.; Depezay, J.-C. Synlett 1999, 1322-1324. (m) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475-4478. (n) Blériot, Y.; Giroult, A.; Mallet, J.-M.; Rodriguez, E.; Vogel, P.; Sinaÿ, P. Tetrahedron: Asymmetry 2002, 13, 2553-2565.
20. For selected references on the synthesis of carbaseptanose and carbaoctanose derivatives, see: (a) Wang, W.; Zhang, Y.; Sollogoub, M.; Sinaÿ, P. Angew. Chem., Int. Ed. 2000, 39, 2466-2467. (b) Wang, W.; Zhang, Y.; Zhou, H.; Blériot, Y.; Sinaÿ, P. Eur. J. Org. Chem. 2001, 1053-1059. (c) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2002, 67, 3705-3717. (d) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2000, 65, 5416-5419. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651-2654. (f) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094-4096. (g) van Hooft, P. A. V.; Litjens, R. E. J. N.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Org. Lett. 2001, 3, 731-733. (h) McNulty, J.; Grunner, V.; Mao, J. Tetrahedron Lett. 2001, 42, 5609-5612. (i) Pearson, A. J.; Katiyar, S. Tetrahedron 2000, 56, 2297-2304. (j) Roy, A.; Chakrabarty, K.; Dutta, P. K.; Bar, N. C.; Basu, N.; Achari, B.; Mandal, S. B. J. Org. Chem. 1999, 64, 2304-2309. (k) Patra, R.; Bar, N. C.; Roy, A.; Achari, B.; Ghoshal, N.; Mandal, S. B. Tetrahedron 1996, 52, 11265-11272. (l) Le Merrer, Y.; Gravier-Pelletier, C.; Maton, W.; Numa, M.; Depezay, J.-C. Synlett 1999, 1322-1324. (m) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475-4478. (n) Blériot, Y.; Giroult, A.; Mallet, J.-M.; Rodriguez, E.; Vogel, P.; Sinaÿ, P. Tetrahedron: Asymmetry 2002, 13, 2553-2565.
21. For selected references on the synthesis of carbaseptanose and carbaoctanose derivatives, see: (a) Wang, W.; Zhang, Y.; Sollogoub, M.; Sinaÿ, P. Angew. Chem., Int. Ed. 2000, 39, 2466-2467. (b) Wang, W.; Zhang, Y.; Zhou, H.; Blériot, Y.; Sinaÿ, P. Eur. J. Org. Chem. 2001, 1053-1059. (c) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2002, 67, 3705-3717. (d) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2000, 65, 5416-5419. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651-2654. (f) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094-4096. (g) van Hooft, P. A. V.; Litjens, R. E. J. N.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Org. Lett. 2001, 3, 731-733. (h) McNulty, J.; Grunner, V.; Mao, J. Tetrahedron Lett. 2001, 42, 5609-5612. (i) Pearson, A. J.; Katiyar, S. Tetrahedron 2000, 56, 2297-2304. (j) Roy, A.; Chakrabarty, K.; Dutta, P. K.; Bar, N. C.; Basu, N.; Achari, B.; Mandal, S. B. J. Org. Chem. 1999, 64, 2304-2309. (k) Patra, R.; Bar, N. C.; Roy, A.; Achari, B.; Ghoshal, N.; Mandal, S. B. Tetrahedron 1996, 52, 11265-11272. (l) Le Merrer, Y.; Gravier-Pelletier, C.; Maton, W.; Numa, M.; Depezay, J.-C. Synlett 1999, 1322-1324. (m) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475-4478. (n) Blériot, Y.; Giroult, A.; Mallet, J.-M.; Rodriguez, E.; Vogel, P.; Sinaÿ, P. Tetrahedron: Asymmetry 2002, 13, 2553-2565.
22. For selected references on the synthesis of carbaseptanose and carbaoctanose derivatives, see: (a) Wang, W.; Zhang, Y.; Sollogoub, M.; Sinaÿ, P. Angew. Chem., Int. Ed. 2000, 39, 2466-2467. (b) Wang, W.; Zhang, Y.; Zhou, H.; Blériot, Y.; Sinaÿ, P. Eur. J. Org. Chem. 2001, 1053-1059. (c) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2002, 67, 3705-3717. (d) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2000, 65, 5416-5419. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651-2654. (f) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094-4096. (g) van Hooft, P. A. V.; Litjens, R. E. J. N.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Org. Lett. 2001, 3, 731-733. (h) McNulty, J.; Grunner, V.; Mao, J. Tetrahedron Lett. 2001, 42, 5609-5612. (i) Pearson, A. J.; Katiyar, S. Tetrahedron 2000, 56, 2297-2304. (j) Roy, A.; Chakrabarty, K.; Dutta, P. K.; Bar, N. C.; Basu, N.; Achari, B.; Mandal, S. B. J. Org. Chem. 1999, 64, 2304-2309. (k) Patra, R.; Bar, N. C.; Roy, A.; Achari, B.; Ghoshal, N.; Mandal, S. B. Tetrahedron 1996, 52, 11265-11272. (l) Le Merrer, Y.; Gravier-Pelletier, C.; Maton, W.; Numa, M.; Depezay, J.-C. Synlett 1999, 1322-1324. (m) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475-4478. (n) Blériot, Y.; Giroult, A.; Mallet, J.-M.; Rodriguez, E.; Vogel, P.; Sinaÿ, P. Tetrahedron: Asymmetry 2002, 13, 2553-2565.
23. For selected references on the synthesis of carbaseptanose and carbaoctanose derivatives, see: (a) Wang, W.; Zhang, Y.; Sollogoub, M.; Sinaÿ, P. Angew. Chem., Int. Ed. 2000, 39, 2466-2467. (b) Wang, W.; Zhang, Y.; Zhou, H.; Blériot, Y.; Sinaÿ, P. Eur. J. Org. Chem. 2001, 1053-1059. (c) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2002, 67, 3705-3717. (d) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2000, 65, 5416-5419. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651-2654. (f) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094-4096. (g) van Hooft, P. A. V.; Litjens, R. E. J. N.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Org. Lett. 2001, 3, 731-733. (h) McNulty, J.; Grunner, V.; Mao, J. Tetrahedron Lett. 2001, 42, 5609-5612. (i) Pearson, A. J.; Katiyar, S. Tetrahedron 2000, 56, 2297-2304. (j) Roy, A.; Chakrabarty, K.; Dutta, P. K.; Bar, N. C.; Basu, N.; Achari, B.; Mandal, S. B. J. Org. Chem. 1999, 64, 2304-2309. (k) Patra, R.; Bar, N. C.; Roy, A.; Achari, B.; Ghoshal, N.; Mandal, S. B. Tetrahedron 1996, 52, 11265-11272. (l) Le Merrer, Y.; Gravier-Pelletier, C.; Maton, W.; Numa, M.; Depezay, J.-C. Synlett 1999, 1322-1324. (m) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475-4478. (n) Blériot, Y.; Giroult, A.; Mallet, J.-M.; Rodriguez, E.; Vogel, P.; Sinaÿ, P. Tetrahedron: Asymmetry 2002, 13, 2553-2565.
24. For selected references on the synthesis of carbaseptanose and carbaoctanose derivatives, see: (a) Wang, W.; Zhang, Y.; Sollogoub, M.; Sinaÿ, P. Angew. Chem., Int. Ed. 2000, 39, 2466-2467. (b) Wang, W.; Zhang, Y.; Zhou, H.; Blériot, Y.; Sinaÿ, P. Eur. J. Org. Chem. 2001, 1053-1059. (c) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2002, 67, 3705-3717. (d) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2000, 65, 5416-5419. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651-2654. (f) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094-4096. (g) van Hooft, P. A. V.; Litjens, R. E. J. N.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Org. Lett. 2001, 3, 731-733. (h) McNulty, J.; Grunner, V.; Mao, J. Tetrahedron Lett. 2001, 42, 5609-5612. (i) Pearson, A. J.; Katiyar, S. Tetrahedron 2000, 56, 2297-2304. (j) Roy, A.; Chakrabarty, K.; Dutta, P. K.; Bar, N. C.; Basu, N.; Achari, B.; Mandal, S. B. J. Org. Chem. 1999, 64, 2304-2309. (k) Patra, R.; Bar, N. C.; Roy, A.; Achari, B.; Ghoshal, N.; Mandal, S. B. Tetrahedron 1996, 52, 11265-11272. (l) Le Merrer, Y.; Gravier-Pelletier, C.; Maton, W.; Numa, M.; Depezay, J.-C. Synlett 1999, 1322-1324. (m) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475-4478. (n) Blériot, Y.; Giroult, A.; Mallet, J.-M.; Rodriguez, E.; Vogel, P.; Sinaÿ, P. Tetrahedron: Asymmetry 2002, 13, 2553-2565.
25. For selected references on the synthesis of carbaseptanose and carbaoctanose derivatives, see: (a) Wang, W.; Zhang, Y.; Sollogoub, M.; Sinaÿ, P. Angew. Chem., Int. Ed. 2000, 39, 2466-2467. (b) Wang, W.; Zhang, Y.; Zhou, H.; Blériot, Y.; Sinaÿ, P. Eur. J. Org. Chem. 2001, 1053-1059. (c) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2002, 67, 3705-3717. (d) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2000, 65, 5416-5419. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651-2654. (f) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094-4096. (g) van Hooft, P. A. V.; Litjens, R. E. J. N.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Org. Lett. 2001, 3, 731-733. (h) McNulty, J.; Grunner, V.; Mao, J. Tetrahedron Lett. 2001, 42, 5609-5612. (i) Pearson, A. J.; Katiyar, S. Tetrahedron 2000, 56, 2297-2304. (j) Roy, A.; Chakrabarty, K.; Dutta, P. K.; Bar, N. C.; Basu, N.; Achari, B.; Mandal, S. B. J. Org. Chem. 1999, 64, 2304-2309. (k) Patra, R.; Bar, N. C.; Roy, A.; Achari, B.; Ghoshal, N.; Mandal, S. B. Tetrahedron 1996, 52, 11265-11272. (l) Le Merrer, Y.; Gravier-Pelletier, C.; Maton, W.; Numa, M.; Depezay, J.-C. Synlett 1999, 1322-1324. (m) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475-4478. (n) Blériot, Y.; Giroult, A.; Mallet, J.-M.; Rodriguez, E.; Vogel, P.; Sinaÿ, P. Tetrahedron: Asymmetry 2002, 13, 2553-2565.
26. For selected references on the synthesis of carbaseptanose and carbaoctanose derivatives, see: (a) Wang, W.; Zhang, Y.; Sollogoub, M.; Sinaÿ, P. Angew. Chem., Int. Ed. 2000, 39, 2466-2467. (b) Wang, W.; Zhang, Y.; Zhou, H.; Blériot, Y.; Sinaÿ, P. Eur. J. Org. Chem. 2001, 1053-1059. (c) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2002, 67, 3705-3717. (d) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2000, 65, 5416-5419. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651-2654. (f) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094-4096. (g) van Hooft, P. A. V.; Litjens, R. E. J. N.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Org. Lett. 2001, 3, 731-733. (h) McNulty, J.; Grunner, V.; Mao, J. Tetrahedron Lett. 2001, 42, 5609-5612. (i) Pearson, A. J.; Katiyar, S. Tetrahedron 2000, 56, 2297-2304. (j) Roy, A.; Chakrabarty, K.; Dutta, P. K.; Bar, N. C.; Basu, N.; Achari, B.; Mandal, S. B. J. Org. Chem. 1999, 64, 2304-2309. (k) Patra, R.; Bar, N. C.; Roy, A.; Achari, B.; Ghoshal, N.; Mandal, S. B. Tetrahedron 1996, 52, 11265-11272. (l) Le Merrer, Y.; Gravier-Pelletier, C.; Maton, W.; Numa, M.; Depezay, J.-C. Synlett 1999, 1322-1324. (m) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475-4478. (n) Blériot, Y.; Giroult, A.; Mallet, J.-M.; Rodriguez, E.; Vogel, P.; Sinaÿ, P. Tetrahedron: Asymmetry 2002, 13, 2553-2565.
27. For selected references on the synthesis of carbaseptanose and carbaoctanose derivatives, see: (a) Wang, W.; Zhang, Y.; Sollogoub, M.; Sinaÿ, P. Angew. Chem., Int. Ed. 2000, 39, 2466-2467. (b) Wang, W.; Zhang, Y.; Zhou, H.; Blériot, Y.; Sinaÿ, P. Eur. J. Org. Chem. 2001, 1053-1059. (c) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2002, 67, 3705-3717. (d) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2000, 65, 5416-5419. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651-2654. (f) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094-4096. (g) van Hooft, P. A. V.; Litjens, R. E. J. N.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Org. Lett. 2001, 3, 731-733. (h) McNulty, J.; Grunner, V.; Mao, J. Tetrahedron Lett. 2001, 42, 5609-5612. (i) Pearson, A. J.; Katiyar, S. Tetrahedron 2000, 56, 2297-2304. (j) Roy, A.; Chakrabarty, K.; Dutta, P. K.; Bar, N. C.; Basu, N.; Achari, B.; Mandal, S. B. J. Org. Chem. 1999, 64, 2304-2309. (k) Patra, R.; Bar, N. C.; Roy, A.; Achari, B.; Ghoshal, N.; Mandal, S. B. Tetrahedron 1996, 52, 11265-11272. (l) Le Merrer, Y.; Gravier-Pelletier, C.; Maton, W.; Numa, M.; Depezay, J.-C. Synlett 1999, 1322-1324. (m) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475-4478. (n) Blériot, Y.; Giroult, A.; Mallet, J.-M.; Rodriguez, E.; Vogel, P.; Sinaÿ, P. Tetrahedron: Asymmetry 2002, 13, 2553-2565.
28. For selected references on the synthesis of carbaseptanose and carbaoctanose derivatives, see: (a) Wang, W.; Zhang, Y.; Sollogoub, M.; Sinaÿ, P. Angew. Chem., Int. Ed. 2000, 39, 2466-2467. (b) Wang, W.; Zhang, Y.; Zhou, H.; Blériot, Y.; Sinaÿ, P. Eur. J. Org. Chem. 2001, 1053-1059. (c) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2002, 67, 3705-3717. (d) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2000, 65, 5416-5419. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651-2654. (f) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094-4096. (g) van Hooft, P. A. V.; Litjens, R. E. J. N.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Org. Lett. 2001, 3, 731-733. (h) McNulty, J.; Grunner, V.; Mao, J. Tetrahedron Lett. 2001, 42, 5609-5612. (i) Pearson, A. J.; Katiyar, S. Tetrahedron 2000, 56, 2297-2304. (j) Roy, A.; Chakrabarty, K.; Dutta, P. K.; Bar, N. C.; Basu, N.; Achari, B.; Mandal, S. B. J. Org. Chem. 1999, 64, 2304-2309. (k) Patra, R.; Bar, N. C.; Roy, A.; Achari, B.; Ghoshal, N.; Mandal, S. B. Tetrahedron 1996, 52, 11265-11272. (l) Le Merrer, Y.; Gravier-Pelletier, C.; Maton, W.; Numa, M.; Depezay, J.-C. Synlett 1999, 1322-1324. (m) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475-4478. (n) Blériot, Y.; Giroult, A.; Mallet, J.-M.; Rodriguez, E.; Vogel, P.; Sinaÿ, P. Tetrahedron: Asymmetry 2002, 13, 2553-2565.
29. (a) Zanardi, F.; Battistini, L.; Marzocchi, L.; Acquotti, D.; Rassu, G.; Pinna, L.; Auzzas, L.; Zambrano, V.; Casiraghi, G. Eur. J. Org. Chem. 2002, 1956-1964.
30. (b) Rassu, G.; Auzzas, L.; Pinna, L.; Zambrano, V.; Battistini, L.; Zanardi, F.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2001, 66, 8070-8075.
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32. For a comprehensive, updated treatise on sugar and carbasugar nomenclature, see: McNaught, A. D. Carbohydr. Res. 1997, 297, 1-92.
33. (a) Casiraghi, G.; Rassu, G.; Zanardi, F.; Battistini, L. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Stamford; 1998; Vol. 3, pp 113-189.
34. (b) Rassu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Chem. Soc. Rev. 2000, 109-118.
35. (c) Rassu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Synlett 1999, 1333-1350.
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37. (a) Mukaiyama, T.; Suzuki, K.; Yamada, T.; Tabusa, F. Tetrahedron 1990, 46, 265-276.
38. (b) Hungerbühler, E.; Seebach, D. Helv. Chim. Acta 1981, 64, 687-702.
39. A handy form of numeration was adopted throughout this text both for the intermediate and target compounds which does not correspond to IUPAC nomenclature. IUPAC nomenclature was, however, adopted in the Supporting Information chapter of the Experimental Section.
40. Caggiano, T. J. In Handbook of Reagents for Organic Synthesis. Oxidizing and Reducing Agents; Burke, S. D., Danheiser, R. L., Eds.; Wiley: Chichester; 1999; pp 246-250.
41. 1H NOE contacts for 11, 17, and 23 are reported in Supporting Information (Tables S1-S3).
42. Hwu, J. R.; Jain, M. L.; Tsay, S.-C.; Hakimelahi, G. H. Tetrahedron Lett. 1996, 37, 2035-2038.
43. (a) Zinner, H.; Brandner, H.; Rembarz, G. Chem. Ber. 1956, 89, 800-813.
44. (b) Zinner, H.; Wittenburg, E.; Rembarz, G. Chem. Ber. 1959, 92, 1614-1617.
45. Rodríguez, A.; Nomen, M.; Spur, B. W.; Godfroid, J. J. Tetrahedron Lett. 1999, 40, 5161-5164.
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52. Contrary to the observations made for its seven-membered analogues 3 and ent-3, cyclooctane 4 showed a strong propensity towards reannulation into the bicyclic lactam. For this reason, compound characterizations were carried out on the hydrochloride salt.
53. A less straightforward attempt to convert intermediate 24 to the corresponding amino-carbasugar via sequential hydrolytic opening (LiOH, aqueous THF) and reduction was frustrated owing to the unpredictable robustness of the C-NH linkage.