Enantioselective synthesis of α-methyl-D-cysteine and lanthionine building blocks via α-methyl-d-serine-β-lactone

Organic Letters

Volumn 5, Issue 7, 2003, Pages 1035-1037

  Smith, Nicole D ^a   Goodman, Murray ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYSTEINE DERIVATIVE; LACTONE DERIVATIVE; LANTHIONINE; ALANINE; ALPHA METHYL D SERINE BETA LACTONE; ALPHA-METHYL-D-SERINE-BETA-LACTONE; CYSTEINE; DRUG DERIVATIVE; LACTONE; SERINE; SULFIDE;

ARTICLE; ENANTIOSELECTIVITY; RING OPENING; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION;

ALANINE; CYSTEINE; LACTONES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; SERINE; SULFIDES;

EID: 0038316202     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034025p     Document Type: Article

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11. This list of references provides examples and is by no means complete: (a) Seebach, D.; Aebi, J. D. Tetrahedron Lett. 1984, 25, 2545-2548. (b) Ito, Y. ; Sawamura, M.; Shirakawa, E.; Hayashizaki, K.; Hayashi, T. Tetrahedron Lett. 1988, 29, 235-238. (c) Colson, P. J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918-5924. (d) Fukuyama, T.; Xu, L. J. Am. Chem. Soc. 1993, 115, 8449-8450. (e) Zembower, D. E.; Gilbert, J. A.; Ames, M. M. J. Med. Chem. 1993, 36, 305-313. (f) Wipf, P.; Venkatraman, S.; Miller, C. P. Tetrahedron Lett. 1995, 36, 3639-3642.
12. This list of references provides examples and is by no means complete: (a) Seebach, D.; Aebi, J. D. Tetrahedron Lett. 1984, 25, 2545-2548. (b) Ito, Y. ; Sawamura, M.; Shirakawa, E.; Hayashizaki, K.; Hayashi, T. Tetrahedron Lett. 1988, 29, 235-238. (c) Colson, P. J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918-5924. (d) Fukuyama, T.; Xu, L. J. Am. Chem. Soc. 1993, 115, 8449-8450. (e) Zembower, D. E.; Gilbert, J. A.; Ames, M. M. J. Med. Chem. 1993, 36, 305-313. (f) Wipf, P.; Venkatraman, S.; Miller, C. P. Tetrahedron Lett. 1995, 36, 3639-3642.
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16. 1H NMR (Supporting Information).
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18. One of the difficulties in the formation of serine lactones is the separation of the lactone from the hydrazine of DIAD by column chromatography. This was not the case with the Boc-α-Me-D-serine-β-lactone where the two compounds could easily be separated by column chromatography.