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Volumn 6, Issue 17, 2004, Pages 2861-2863

Sphingolipid synthesis via olefin cross metathesis: Preparation of a differentially protected building block and application to the synthesis of D-erythro-ceramide

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CERAMIDE DERIVATIVE; DEXTRO ERYTHRO CERAMIDE; SPHINGOLIPID; UNCLASSIFIED DRUG;

EID: 4444382295     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049183a     Document Type: Article
Times cited : (68)

References (33)
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    • For some recent syntheses of ceramide/sphingolipids, see: (a) Jeong, L.-Y.; Lee, J. H.; Lee, B. W.; Kim, J. H.; Park, K. H. Bull. Korean Chem. Soc. 2003, 24, 617-622. (b) Milne, J. E.; Jarowicki, K.; Kocienski, P. J.; Alonso, J. Chem. Commun. 2002, 426-427. (c) Lees, W. J.; Gargano, J. M. Tetrahedron Lett. 2001, 42, 5845-5847. (d) Lee, J.-M.; Lim, H.-S.; Chung, S.-K. Tetrahedron: Asymmetry 2002, 13, 343-347. (e) Bittman, R.; Chun, J.; Li, G.; Byun, H.-S. Tetrahedron Lett. 2002, 43, 375-377.
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    • For some recent syntheses of ceramide/sphingolipids, see: (a) Jeong, L.-Y.; Lee, J. H.; Lee, B. W.; Kim, J. H.; Park, K. H. Bull. Korean Chem. Soc. 2003, 24, 617-622. (b) Milne, J. E.; Jarowicki, K.; Kocienski, P. J.; Alonso, J. Chem. Commun. 2002, 426-427. (c) Lees, W. J.; Gargano, J. M. Tetrahedron Lett. 2001, 42, 5845-5847. (d) Lee, J.-M.; Lim, H.-S.; Chung, S.-K. Tetrahedron: Asymmetry 2002, 13, 343-347. (e) Bittman, R.; Chun, J.; Li, G.; Byun, H.-S. Tetrahedron Lett. 2002, 43, 375-377.
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    • For some recent syntheses of ceramide/sphingolipids, see: (a) Jeong, L.-Y.; Lee, J. H.; Lee, B. W.; Kim, J. H.; Park, K. H. Bull. Korean Chem. Soc. 2003, 24, 617-622. (b) Milne, J. E.; Jarowicki, K.; Kocienski, P. J.; Alonso, J. Chem. Commun. 2002, 426-427. (c) Lees, W. J.; Gargano, J. M. Tetrahedron Lett. 2001, 42, 5845-5847. (d) Lee, J.-M.; Lim, H.-S.; Chung, S.-K. Tetrahedron: Asymmetry 2002, 13, 343-347. (e) Bittman, R.; Chun, J.; Li, G.; Byun, H.-S. Tetrahedron Lett. 2002, 43, 375-377.
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    • For some recent syntheses of ceramide/sphingolipids, see: (a) Jeong, L.-Y.; Lee, J. H.; Lee, B. W.; Kim, J. H.; Park, K. H. Bull. Korean Chem. Soc. 2003, 24, 617-622. (b) Milne, J. E.; Jarowicki, K.; Kocienski, P. J.; Alonso, J. Chem. Commun. 2002, 426-427. (c) Lees, W. J.; Gargano, J. M. Tetrahedron Lett. 2001, 42, 5845-5847. (d) Lee, J.-M.; Lim, H.-S.; Chung, S.-K. Tetrahedron: Asymmetry 2002, 13, 343-347. (e) Bittman, R.; Chun, J.; Li, G.; Byun, H.-S. Tetrahedron Lett. 2002, 43, 375-377.
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    • note
    • Gargano and Lees have reported the preparation of an orthogonally protected sphingosine with the main carbon chain already installed; See ref 3c.
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    • During the preparation of this manuscript, we became aware of a report by Torssell and Somfai describing a cross metathesis approach to sphingosines using a different five-carbon building block. See: Torssell, S.; Somfai, P. Org. Biomol. Chem. 2004, 2, 1643-1646. A patent (WO 03/101937) by Rich and Bundle refers to olefin cross metathesis reactions of similar structures, but reduction to practice is not disclosed in the patent.
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    • During their synthesis of sphingolipids, Nugent and Hudlicky noted that reaction of azido aldehydes with Wittig reagents also resulted in reaction of the ylide at the azide functionality. See: Nugent, T.; Hudlicky, T. J. Org. Chem. 1998, 63, 510-520. We have found that careful addition of the ylide to the aldehyde at -78°C results in clean olefination, while higher temperatures give rise to products derived from both olefination and reaction at the azide.
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    • note
    • The thiotrityl alkene was prepared from the known alkenol. Details are provided in Supporting Information.
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    • note
    • The isolated yields for the cross metathesis reactions of the acetyl, palmitoyl, and benzoyl amides of 8 with hexadecene range from 71% to 92%. The pivaloyl amide undergoes cross metathesis with hexadecene less efficiently, affording the product in only 37% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.