Linchpin construction of unsymmetrical 1,4-alkynediols

Journal of Organic Chemistry

Volumn 67, Issue 23, 2002, Pages 8273-8275

  Taber, Douglass F ^a   Storck, Pierre H ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PROTECTING GROUPS;

ADDITION REACTIONS; KETONES; LITHIUM; SOLUTIONS;

ALDEHYDES;

ALDEHYDE; ALKYNE; CYCLOPENTENONE DERIVATIVE; FURAN DERIVATIVE; KETONE; LITHIUM DERIVATIVE; PYRROLE DERIVATIVE; SILANE DERIVATIVE; ALCOHOL DERIVATIVE; NONSTEROID ANTIINFLAMMATORY AGENT;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; CHEMISTRY;

ALCOHOLS; ALDEHYDES; ALKYNES; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; KETONES;

EID: 0037111608     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020486x     Document Type: Article

References (17)

1. Janusz, J. M.; Young, P. A.; Ridgeway, J. M.; Scherz, M. W.; Enzweiler, K.; Wu, L. I.; Gan, L.; Chen, J.; Kellstein, D. E.; Green, S. A.; Tulich, J. L.; Rosario-Jansen, T.; Magrisso, I. J.; Wehmeyer, K. R.; Kuhlenbeck, D. L.; Eichhold, T. H.; Dobson, R. L. M. J. Med. Chem. 1998, 41, 3515-3529.
2. 2: Chabaud, B.; Sharpless, B. K. J. Org. Chem. 1979, 44, 4202-4203.
3. 2: Chabaud, B.; Sharpless, B. K. J. Org. Chem. 1979, 44, 4202-4203.
4. 2: Chabaud, B.; Sharpless, B. K. J. Org. Chem. 1979, 44, 4202-4203.
5. 2: Chabaud, B.; Sharpless, B. K. J. Org. Chem. 1979, 44, 4202-4203.
6. 2: Chabaud, B.; Sharpless, B. K. J. Org. Chem. 1979, 44, 4202-4203.
7. 2: Chabaud, B.; Sharpless, B. K. J. Org. Chem. 1979, 44, 4202-4203.
8. 2: Chabaud, B.; Sharpless, B. K. J. Org. Chem. 1979, 44, 4202-4203.
9. For the stereoselective synthesis of unsymmetrical 1,4-alkynediols, see the following: (a) By a [2,3] Wittig rearrangement of a propargylic allylic ether: Marshall, J. A.; Jenson, T. M.; DeHoff, B. S. J. Org. Chem. 1987, 52, 3860-3866. (b) From the zinc triflate mediated addition of a propargylic alcohol to an aldehyde: Boyall, D.; Lopez, F.; Sasaki, H.; Frantz, D.; Carreira, E. M. Org. Lett. 2000, 2, 4233-4236. (c) From a 1-chloroalkyl epoxide precursor: Li, W.-D.; Li, Y.-L.; Li, Y. J. Chin. Chem. Soc. 1995, 42, 701-708.
10. For the stereoselective synthesis of unsymmetrical 1,4-alkynediols, see the following: (a) By a [2,3] Wittig rearrangement of a propargylic allylic ether: Marshall, J. A.; Jenson, T. M.; DeHoff, B. S. J. Org. Chem. 1987, 52, 3860-3866. (b) From the zinc triflate mediated addition of a propargylic alcohol to an aldehyde: Boyall, D.; Lopez, F.; Sasaki, H.; Frantz, D.; Carreira, E. M. Org. Lett. 2000, 2, 4233-4236. (c) From a 1-chloroalkyl epoxide precursor: Li, W.-D.; Li, Y.-L.; Li, Y. J. Chin. Chem. Soc. 1995, 42, 701-708.
11. For the stereoselective synthesis of unsymmetrical 1,4-alkynediols, see the following: (a) By a [2,3] Wittig rearrangement of a propargylic allylic ether: Marshall, J. A.; Jenson, T. M.; DeHoff, B. S. J. Org. Chem. 1987, 52, 3860-3866. (b) From the zinc triflate mediated addition of a propargylic alcohol to an aldehyde: Boyall, D.; Lopez, F.; Sasaki, H.; Frantz, D.; Carreira, E. M. Org. Lett. 2000, 2, 4233-4236. (c) From a 1-chloroalkyl epoxide precursor: Li, W.-D.; Li, Y.-L.; Li, Y. J. Chin. Chem. Soc. 1995, 42, 701-708.
12. For a diastereoselective synthesis of unsymmetrical 1,4-alkynediols by the Lewis acid mediated addition of a metal acetylide to an acetal, see Yamamoto, Y.; Abe, H.; Nishii, S.; Yamada, J-i. J. Chem. Soc., Perkin Trans. 1 1991, 3253.
13. Holmes, A. B.; Jennings-White, C. L. D.; Schulthess, A. H.; Akinde, B.; Walton, D. R. M. J. Chem. Soc., Chem. Commun. 1979, 19, 840-842
14. Lu, X.; Ji, J.; Ma, D.; Shen, W. J. Org. Chem. 1991, 56, 5774-5778.
15. Ariza, X.; Garcia, J.; Lopez, M.; Montserrat, L. Synlett 2001, 120-122.
16. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925.
17. Mukaiyama, T.; Shiina, I.; Sakata, K.; Emura, T.; Seto, K.; Saitoh, M. Chem. Lett. 1995, 3, 179-180.