An Efficient Chiral Moderator Prepared from Inexpensive (+)-3-Carene:  Synthesis of the HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitor DPC 963

An Efficient Chiral Moderator Prepared from Inexpensive (+)-3-Carene:  Synthesis of the HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitor DPC 963

The β-amino alcohol 4β-morpholinocaran-3α-ol is prepared by addition of morpholine to α-3,4-epoxycarane utilizing anhydrous magnesium bromide as Lewis acid promoter. The enantiopure amino alcohol is uniquely effective as a chiral moderator for the addition of lithium cyclopropylacetylide to an unpro...

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Veröffentlicht in:Organic letters 2000-10, Vol.2 (20), p.3119-3121
Hauptverfasser: Kauffman, Goss S, Harris, Gregory D, Dorow, Roberta L, Stone, Benjamin R. P, Parsons, Rodney L, Pesti, Jaan A, Magnus, Nicholas A, Fortunak, Joseph M, Confalone, Pat N, Nugent, William A
Format: Artikel
Sprache:eng
Schlagworte:
HIV-1 - enzymology
Quinolones - chemical synthesis
Reverse Transcriptase Inhibitors - chemical synthesis
Stereoisomerism
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Zusammenfassung:The β-amino alcohol 4β-morpholinocaran-3α-ol is prepared by addition of morpholine to α-3,4-epoxycarane utilizing anhydrous magnesium bromide as Lewis acid promoter. The enantiopure amino alcohol is uniquely effective as a chiral moderator for the addition of lithium cyclopropylacetylide to an unprotected N-acylketimine. This reaction provides an efficient route to the second generation NNRTI drug candidate DPC 963.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol006321x