Stereoselective synthesis of alkynyl C-2-deoxy-β-D-ribofuranosides via intramolecular Nicholas reaction: A versatile building block for nonnatural C-nucleosides

Organic Letters

Volumn 5, Issue 5, 2003, Pages 625-628

  Takase, Masayoshi ^c   Morikawa, Tomoyuki ^b   Abe, Hajime ^b   Inouye, Masahiko ^a,b  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b UNIVERSITY OF TOYAMA   (Japan)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYL GROUP; BENZYL DERIVATIVE; C NUCLEOSIDE; COBALT; FURAN DERIVATIVE; IODINE; LITHIUM DERIVATIVE; NUCLEOSIDE DERIVATIVE; REAGENT; ALKYNE; DEOXYRIBONUCLEOSIDE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS;

ARTICLE; CATALYSIS; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOSELECTIVITY; MITSUNOBU REACTION; PHARMACOPHORE; REACTION ANALYSIS; RING OPENING; STEREOCHEMISTRY; STRUCTURE ANALYSIS; THERMODYNAMICS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKYNES; CYCLIZATION; DEOXYRIBONUCLEOSIDES; INDICATORS AND REAGENTS; STEREOISOMERISM;

EID: 0038482451     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027210w     Document Type: Article

References (36)

1. Recent books and reviews: (a) Simons, C. Nucleoside Mimetics: Their Chemistry and Biological Properties; Gordon and Breach: Amsterdam, 2001. (b) Togo, H.; He, W.; Waki, Y.; Yokoyama, M. Synlett 1998, 700-717. (c) Levy, D. E. ; Tang, C. The Chemistry of C-Glycosides; Pergamon: Oxford, 1995. (d) Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, FL, 1995. (e) Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20. (f) Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599.
2. Recent books and reviews: (a) Simons, C. Nucleoside Mimetics: Their Chemistry and Biological Properties; Gordon and Breach: Amsterdam, 2001. (b) Togo, H.; He, W.; Waki, Y.; Yokoyama, M. Synlett 1998, 700-717. (c) Levy, D. E. ; Tang, C. The Chemistry of C-Glycosides; Pergamon: Oxford, 1995. (d) Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, FL, 1995. (e) Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20. (f) Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599.
3. Recent books and reviews: (a) Simons, C. Nucleoside Mimetics: Their Chemistry and Biological Properties; Gordon and Breach: Amsterdam, 2001. (b) Togo, H.; He, W.; Waki, Y.; Yokoyama, M. Synlett 1998, 700-717. (c) Levy, D. E. ; Tang, C. The Chemistry of C-Glycosides; Pergamon: Oxford, 1995. (d) Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, FL, 1995. (e) Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20. (f) Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599.
4. Recent books and reviews: (a) Simons, C. Nucleoside Mimetics: Their Chemistry and Biological Properties; Gordon and Breach: Amsterdam, 2001. (b) Togo, H.; He, W.; Waki, Y.; Yokoyama, M. Synlett 1998, 700-717. (c) Levy, D. E. ; Tang, C. The Chemistry of C-Glycosides; Pergamon: Oxford, 1995. (d) Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, FL, 1995. (e) Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20. (f) Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599.
5. Recent books and reviews: (a) Simons, C. Nucleoside Mimetics: Their Chemistry and Biological Properties; Gordon and Breach: Amsterdam, 2001. (b) Togo, H.; He, W.; Waki, Y.; Yokoyama, M. Synlett 1998, 700-717. (c) Levy, D. E. ; Tang, C. The Chemistry of C-Glycosides; Pergamon: Oxford, 1995. (d) Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, FL, 1995. (e) Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20. (f) Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599.
6. Recent books and reviews: (a) Simons, C. Nucleoside Mimetics: Their Chemistry and Biological Properties; Gordon and Breach: Amsterdam, 2001. (b) Togo, H.; He, W.; Waki, Y.; Yokoyama, M. Synlett 1998, 700-717. (c) Levy, D. E. ; Tang, C. The Chemistry of C-Glycosides; Pergamon: Oxford, 1995. (d) Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, FL, 1995. (e) Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20. (f) Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599.
7. Recent reviews: (a) Isobe, M.; Nishizawa, R.; Hosokawa, S.; Nishikawa, T. Chem. Commun. 1998, 2665-2676. (b) Isobe, M. J. Synth. Org. Chem., Jpn. 1994, 52, 968-979. Some examples were also seen in ref 1.
8. Recent reviews: (a) Isobe, M.; Nishizawa, R.; Hosokawa, S.; Nishikawa, T. Chem. Commun. 1998, 2665-2676. (b) Isobe, M. J. Synth. Org. Chem., Jpn. 1994, 52, 968-979. Some examples were also seen in ref 1.
9. Wamhoff, H.; Warnecke, H. ARKIVOC (online computer file) 2001, 2, 1085-1090.
10. On the other hand, various methods have been reported for the synthesis of alkynyl C-β-D-ribofuranosides: (a) Buchanan, J. G.; Edgar, A. R.; Power, M. J. J. Chem. Soc., Perkin Trans. 1 1974, 1943-1949. Buchanan, J. G.; Dunn, A. D.; Edgar, A. R. J. Chem. Soc., Perkin Trans. 1 1975, 1191-1200. (b) Arakawa, K.; Miyasaka, T.; Hamamichi, N. Chem. Lett. 1976, 1119-1122. Hamamichi, N.; Miyasaka, T.; Arakawa, K. Chem. Pharm. Bull. 1978, 26, 898-907. (c) De Las Heras, F. G.; Tam, S. Y.-K.; Klein, R. S.; Fox, J. J. J. Org. Chem. 1976, 41, 84-90. Tam, S. Y.-K.; Klein, R. S.; De Las Heras, F. G.; Fox, J. J. J. Org. Chem. 1979, 44, 4854-4862. (d) Alonso, G.; Garcia-Lopez, M. T.; Garcia-Muñoz, G.; Madroñero, R. An. Quim. 1976, 72, 987-990. (e) Gupta, C. M.; Jones, G. H.; Moffatt, J. G. J. Org. Chem. 1976, 41, 3000-3009. (f) Zhai, D.; Zhai, W.; Williams, R. M. J. Am. Chem. Soc. 1988, 110, 2501-2505. (g) Rycroft, A. D.; Singh, G.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1995, 2667-2668. (h) Maqbool, Z.; Hasan, M.; Pott, K. T.; Malik, A.; Nizami, T. A.; Voelter, W. Z. Naturforsch 1997, 52b, 1383-1392.
11. On the other hand, various methods have been reported for the synthesis of alkynyl C-β-D-ribofuranosides: (a) Buchanan, J. G.; Edgar, A. R.; Power, M. J. J. Chem. Soc., Perkin Trans. 1 1974, 1943-1949. Buchanan, J. G.; Dunn, A. D.; Edgar, A. R. J. Chem. Soc., Perkin Trans. 1 1975, 1191-1200. (b) Arakawa, K.; Miyasaka, T.; Hamamichi, N. Chem. Lett. 1976, 1119-1122. Hamamichi, N.; Miyasaka, T.; Arakawa, K. Chem. Pharm. Bull. 1978, 26, 898-907. (c) De Las Heras, F. G.; Tam, S. Y.-K.; Klein, R. S.; Fox, J. J. J. Org. Chem. 1976, 41, 84-90. Tam, S. Y.-K.; Klein, R. S.; De Las Heras, F. G.; Fox, J. J. J. Org. Chem. 1979, 44, 4854-4862. (d) Alonso, G.; Garcia-Lopez, M. T.; Garcia-Muñoz, G.; Madroñero, R. An. Quim. 1976, 72, 987-990. (e) Gupta, C. M.; Jones, G. H.; Moffatt, J. G. J. Org. Chem. 1976, 41, 3000-3009. (f) Zhai, D.; Zhai, W.; Williams, R. M. J. Am. Chem. Soc. 1988, 110, 2501-2505. (g) Rycroft, A. D.; Singh, G.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1995, 2667-2668. (h) Maqbool, Z.; Hasan, M.; Pott, K. T.; Malik, A.; Nizami, T. A.; Voelter, W. Z. Naturforsch 1997, 52b, 1383-1392.
12. On the other hand, various methods have been reported for the synthesis of alkynyl C-β-D-ribofuranosides: (a) Buchanan, J. G.; Edgar, A. R.; Power, M. J. J. Chem. Soc., Perkin Trans. 1 1974, 1943-1949. Buchanan, J. G.; Dunn, A. D.; Edgar, A. R. J. Chem. Soc., Perkin Trans. 1 1975, 1191-1200. (b) Arakawa, K.; Miyasaka, T.; Hamamichi, N. Chem. Lett. 1976, 1119-1122. Hamamichi, N.; Miyasaka, T.; Arakawa, K. Chem. Pharm. Bull. 1978, 26, 898-907. (c) De Las Heras, F. G.; Tam, S. Y.-K.; Klein, R. S.; Fox, J. J. J. Org. Chem. 1976, 41, 84-90. Tam, S. Y.-K.; Klein, R. S.; De Las Heras, F. G.; Fox, J. J. J. Org. Chem. 1979, 44, 4854-4862. (d) Alonso, G.; Garcia-Lopez, M. T.; Garcia-Muñoz, G.; Madroñero, R. An. Quim. 1976, 72, 987-990. (e) Gupta, C. M.; Jones, G. H.; Moffatt, J. G. J. Org. Chem. 1976, 41, 3000-3009. (f) Zhai, D.; Zhai, W.; Williams, R. M. J. Am. Chem. Soc. 1988, 110, 2501-2505. (g) Rycroft, A. D.; Singh, G.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1995, 2667-2668. (h) Maqbool, Z.; Hasan, M.; Pott, K. T.; Malik, A.; Nizami, T. A.; Voelter, W. Z. Naturforsch 1997, 52b, 1383-1392.
13. On the other hand, various methods have been reported for the synthesis of alkynyl C-β-D-ribofuranosides: (a) Buchanan, J. G.; Edgar, A. R.; Power, M. J. J. Chem. Soc., Perkin Trans. 1 1974, 1943-1949. Buchanan, J. G.; Dunn, A. D.; Edgar, A. R. J. Chem. Soc., Perkin Trans. 1 1975, 1191-1200. (b) Arakawa, K.; Miyasaka, T.; Hamamichi, N. Chem. Lett. 1976, 1119-1122. Hamamichi, N.; Miyasaka, T.; Arakawa, K. Chem. Pharm. Bull. 1978, 26, 898-907. (c) De Las Heras, F. G.; Tam, S. Y.-K.; Klein, R. S.; Fox, J. J. J. Org. Chem. 1976, 41, 84-90. Tam, S. Y.-K.; Klein, R. S.; De Las Heras, F. G.; Fox, J. J. J. Org. Chem. 1979, 44, 4854-4862. (d) Alonso, G.; Garcia-Lopez, M. T.; Garcia-Muñoz, G.; Madroñero, R. An. Quim. 1976, 72, 987-990. (e) Gupta, C. M.; Jones, G. H.; Moffatt, J. G. J. Org. Chem. 1976, 41, 3000-3009. (f) Zhai, D.; Zhai, W.; Williams, R. M. J. Am. Chem. Soc. 1988, 110, 2501-2505. (g) Rycroft, A. D.; Singh, G.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1995, 2667-2668. (h) Maqbool, Z.; Hasan, M.; Pott, K. T.; Malik, A.; Nizami, T. A.; Voelter, W. Z. Naturforsch 1997, 52b, 1383-1392.
14. On the other hand, various methods have been reported for the synthesis of alkynyl C-β-D-ribofuranosides: (a) Buchanan, J. G.; Edgar, A. R.; Power, M. J. J. Chem. Soc., Perkin Trans. 1 1974, 1943-1949. Buchanan, J. G.; Dunn, A. D.; Edgar, A. R. J. Chem. Soc., Perkin Trans. 1 1975, 1191-1200. (b) Arakawa, K.; Miyasaka, T.; Hamamichi, N. Chem. Lett. 1976, 1119-1122. Hamamichi, N.; Miyasaka, T.; Arakawa, K. Chem. Pharm. Bull. 1978, 26, 898-907. (c) De Las Heras, F. G.; Tam, S. Y.-K.; Klein, R. S.; Fox, J. J. J. Org. Chem. 1976, 41, 84-90. Tam, S. Y.-K.; Klein, R. S.; De Las Heras, F. G.; Fox, J. J. J. Org. Chem. 1979, 44, 4854-4862. (d) Alonso, G.; Garcia-Lopez, M. T.; Garcia-Muñoz, G.; Madroñero, R. An. Quim. 1976, 72, 987-990. (e) Gupta, C. M.; Jones, G. H.; Moffatt, J. G. J. Org. Chem. 1976, 41, 3000-3009. (f) Zhai, D.; Zhai, W.; Williams, R. M. J. Am. Chem. Soc. 1988, 110, 2501-2505. (g) Rycroft, A. D.; Singh, G.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1995, 2667-2668. (h) Maqbool, Z.; Hasan, M.; Pott, K. T.; Malik, A.; Nizami, T. A.; Voelter, W. Z. Naturforsch 1997, 52b, 1383-1392.
15. On the other hand, various methods have been reported for the synthesis of alkynyl C-β-D-ribofuranosides: (a) Buchanan, J. G.; Edgar, A. R.; Power, M. J. J. Chem. Soc., Perkin Trans. 1 1974, 1943-1949. Buchanan, J. G.; Dunn, A. D.; Edgar, A. R. J. Chem. Soc., Perkin Trans. 1 1975, 1191-1200. (b) Arakawa, K.; Miyasaka, T.; Hamamichi, N. Chem. Lett. 1976, 1119-1122. Hamamichi, N.; Miyasaka, T.; Arakawa, K. Chem. Pharm. Bull. 1978, 26, 898-907. (c) De Las Heras, F. G.; Tam, S. Y.-K.; Klein, R. S.; Fox, J. J. J. Org. Chem. 1976, 41, 84-90. Tam, S. Y.-K.; Klein, R. S.; De Las Heras, F. G.; Fox, J. J. J. Org. Chem. 1979, 44, 4854-4862. (d) Alonso, G.; Garcia-Lopez, M. T.; Garcia-Muñoz, G.; Madroñero, R. An. Quim. 1976, 72, 987-990. (e) Gupta, C. M.; Jones, G. H.; Moffatt, J. G. J. Org. Chem. 1976, 41, 3000-3009. (f) Zhai, D.; Zhai, W.; Williams, R. M. J. Am. Chem. Soc. 1988, 110, 2501-2505. (g) Rycroft, A. D.; Singh, G.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1995, 2667-2668. (h) Maqbool, Z.; Hasan, M.; Pott, K. T.; Malik, A.; Nizami, T. A.; Voelter, W. Z. Naturforsch 1997, 52b, 1383-1392.
16. On the other hand, various methods have been reported for the synthesis of alkynyl C-β-D-ribofuranosides: (a) Buchanan, J. G.; Edgar, A. R.; Power, M. J. J. Chem. Soc., Perkin Trans. 1 1974, 1943-1949. Buchanan, J. G.; Dunn, A. D.; Edgar, A. R. J. Chem. Soc., Perkin Trans. 1 1975, 1191-1200. (b) Arakawa, K.; Miyasaka, T.; Hamamichi, N. Chem. Lett. 1976, 1119-1122. Hamamichi, N.; Miyasaka, T.; Arakawa, K. Chem. Pharm. Bull. 1978, 26, 898-907. (c) De Las Heras, F. G.; Tam, S. Y.-K.; Klein, R. S.; Fox, J. J. J. Org. Chem. 1976, 41, 84-90. Tam, S. Y.-K.; Klein, R. S.; De Las Heras, F. G.; Fox, J. J. J. Org. Chem. 1979, 44, 4854-4862. (d) Alonso, G.; Garcia-Lopez, M. T.; Garcia-Muñoz, G.; Madroñero, R. An. Quim. 1976, 72, 987-990. (e) Gupta, C. M.; Jones, G. H.; Moffatt, J. G. J. Org. Chem. 1976, 41, 3000-3009. (f) Zhai, D.; Zhai, W.; Williams, R. M. J. Am. Chem. Soc. 1988, 110, 2501-2505. (g) Rycroft, A. D.; Singh, G.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1995, 2667-2668. (h) Maqbool, Z.; Hasan, M.; Pott, K. T.; Malik, A.; Nizami, T. A.; Voelter, W. Z. Naturforsch 1997, 52b, 1383-1392.
17. On the other hand, various methods have been reported for the synthesis of alkynyl C-β-D-ribofuranosides: (a) Buchanan, J. G.; Edgar, A. R.; Power, M. J. J. Chem. Soc., Perkin Trans. 1 1974, 1943-1949. Buchanan, J. G.; Dunn, A. D.; Edgar, A. R. J. Chem. Soc., Perkin Trans. 1 1975, 1191-1200. (b) Arakawa, K.; Miyasaka, T.; Hamamichi, N. Chem. Lett. 1976, 1119-1122. Hamamichi, N.; Miyasaka, T.; Arakawa, K. Chem. Pharm. Bull. 1978, 26, 898-907. (c) De Las Heras, F. G.; Tam, S. Y.-K.; Klein, R. S.; Fox, J. J. J. Org. Chem. 1976, 41, 84-90. Tam, S. Y.-K.; Klein, R. S.; De Las Heras, F. G.; Fox, J. J. J. Org. Chem. 1979, 44, 4854-4862. (d) Alonso, G.; Garcia-Lopez, M. T.; Garcia-Muñoz, G.; Madroñero, R. An. Quim. 1976, 72, 987-990. (e) Gupta, C. M.; Jones, G. H.; Moffatt, J. G. J. Org. Chem. 1976, 41, 3000-3009. (f) Zhai, D.; Zhai, W.; Williams, R. M. J. Am. Chem. Soc. 1988, 110, 2501-2505. (g) Rycroft, A. D.; Singh, G.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1995, 2667-2668. (h) Maqbool, Z.; Hasan, M.; Pott, K. T.; Malik, A.; Nizami, T. A.; Voelter, W. Z. Naturforsch 1997, 52b, 1383-1392.
18. On the other hand, various methods have been reported for the synthesis of alkynyl C-β-D-ribofuranosides: (a) Buchanan, J. G.; Edgar, A. R.; Power, M. J. J. Chem. Soc., Perkin Trans. 1 1974, 1943-1949. Buchanan, J. G.; Dunn, A. D.; Edgar, A. R. J. Chem. Soc., Perkin Trans. 1 1975, 1191-1200. (b) Arakawa, K.; Miyasaka, T.; Hamamichi, N. Chem. Lett. 1976, 1119-1122. Hamamichi, N.; Miyasaka, T.; Arakawa, K. Chem. Pharm. Bull. 1978, 26, 898-907. (c) De Las Heras, F. G.; Tam, S. Y.-K.; Klein, R. S.; Fox, J. J. J. Org. Chem. 1976, 41, 84-90. Tam, S. Y.-K.; Klein, R. S.; De Las Heras, F. G.; Fox, J. J. J. Org. Chem. 1979, 44, 4854-4862. (d) Alonso, G.; Garcia-Lopez, M. T.; Garcia-Muñoz, G.; Madroñero, R. An. Quim. 1976, 72, 987-990. (e) Gupta, C. M.; Jones, G. H.; Moffatt, J. G. J. Org. Chem. 1976, 41, 3000-3009. (f) Zhai, D.; Zhai, W.; Williams, R. M. J. Am. Chem. Soc. 1988, 110, 2501-2505. (g) Rycroft, A. D.; Singh, G.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1995, 2667-2668. (h) Maqbool, Z.; Hasan, M.; Pott, K. T.; Malik, A.; Nizami, T. A.; Voelter, W. Z. Naturforsch 1997, 52b, 1383-1392.
19. On the other hand, various methods have been reported for the synthesis of alkynyl C-β-D-ribofuranosides: (a) Buchanan, J. G.; Edgar, A. R.; Power, M. J. J. Chem. Soc., Perkin Trans. 1 1974, 1943-1949. Buchanan, J. G.; Dunn, A. D.; Edgar, A. R. J. Chem. Soc., Perkin Trans. 1 1975, 1191-1200. (b) Arakawa, K.; Miyasaka, T.; Hamamichi, N. Chem. Lett. 1976, 1119-1122. Hamamichi, N.; Miyasaka, T.; Arakawa, K. Chem. Pharm. Bull. 1978, 26, 898-907. (c) De Las Heras, F. G.; Tam, S. Y.-K.; Klein, R. S.; Fox, J. J. J. Org. Chem. 1976, 41, 84-90. Tam, S. Y.-K.; Klein, R. S.; De Las Heras, F. G.; Fox, J. J. J. Org. Chem. 1979, 44, 4854-4862. (d) Alonso, G.; Garcia-Lopez, M. T.; Garcia-Muñoz, G.; Madroñero, R. An. Quim. 1976, 72, 987-990. (e) Gupta, C. M.; Jones, G. H.; Moffatt, J. G. J. Org. Chem. 1976, 41, 3000-3009. (f) Zhai, D.; Zhai, W.; Williams, R. M. J. Am. Chem. Soc. 1988, 110, 2501-2505. (g) Rycroft, A. D.; Singh, G.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1995, 2667-2668. (h) Maqbool, Z.; Hasan, M.; Pott, K. T.; Malik, A.; Nizami, T. A.; Voelter, W. Z. Naturforsch 1997, 52b, 1383-1392.
20. On the other hand, various methods have been reported for the synthesis of alkynyl C-β-D-ribofuranosides: (a) Buchanan, J. G.; Edgar, A. R.; Power, M. J. J. Chem. Soc., Perkin Trans. 1 1974, 1943-1949. Buchanan, J. G.; Dunn, A. D.; Edgar, A. R. J. Chem. Soc., Perkin Trans. 1 1975, 1191-1200. (b) Arakawa, K.; Miyasaka, T.; Hamamichi, N. Chem. Lett. 1976, 1119-1122. Hamamichi, N.; Miyasaka, T.; Arakawa, K. Chem. Pharm. Bull. 1978, 26, 898-907. (c) De Las Heras, F. G.; Tam, S. Y.-K.; Klein, R. S.; Fox, J. J. J. Org. Chem. 1976, 41, 84-90. Tam, S. Y.-K.; Klein, R. S.; De Las Heras, F. G.; Fox, J. J. J. Org. Chem. 1979, 44, 4854-4862. (d) Alonso, G.; Garcia-Lopez, M. T.; Garcia-Muñoz, G.; Madroñero, R. An. Quim. 1976, 72, 987-990. (e) Gupta, C. M.; Jones, G. H.; Moffatt, J. G. J. Org. Chem. 1976, 41, 3000-3009. (f) Zhai, D.; Zhai, W.; Williams, R. M. J. Am. Chem. Soc. 1988, 110, 2501-2505. (g) Rycroft, A. D.; Singh, G.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1995, 2667-2668. (h) Maqbool, Z.; Hasan, M.; Pott, K. T.; Malik, A.; Nizami, T. A.; Voelter, W. Z. Naturforsch 1997, 52b, 1383-1392.
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23. Reviews for Mitsunobu reaction: Mitsunobu, O. Synthesis 1981, 1-28. Hughes, D. L. In Organic Reaction; Paquette, L. A., Ed.; John Wiley: New York, 1992; Vol. 42, pp 335-656.
24. Weizman, H.; Tor, Y. J. Am. Chem. Soc. 2001, 123, 3375-3376.
25. See Supporting Information.
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31. 8 (ca. 0.2 equiv) was added to preserve 6a from decomposition.
32. Isobe et al. reported similar phenomena in the cases of the cobalt complexes of the alkynyl C-pyranose ring: see ref 2.
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