Concepedia

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

Goss S. Kauffman, Gregory D. Harris, Roberta L. Dorow, Benjamin R. P. Stone, Rodney L. Parsons, Jaan A. Pesti, Nicholas A. Magnus, Joseph Fortunak, Pat N. Confalone, William A. Nugent

Organic Letters · 2000 · 193 citations · 7 references

DOI

Concepts

Abstract

The beta-amino alcohol 4 beta-morpholinocaran-3 alpha-ol is prepared by addition of morpholine to alpha-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.

References

7

Lithium Alkoxides of Cinchona Alkaloids as Chiral Controllers for Enantioselective Acetylide Addition to Cyclic N-Acyl Ketimines

Mark A. Huffman, Nobuyoshi Yasuda, Ann E. DeCamp et al. · The Journal of Organic Chemistry · 1995 · 258 citations

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Practical Asymmetric Synthesis of Efavirenz (DMP 266), an HIV-1 Reverse Transcriptase Inhibitor

Michael E. Pierce, Rodney L. Parsons, Lilian Radesca et al. · The Journal of Organic Chemistry · 1998 · 215 citations

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Lithium Ephedrate-Mediated Addition of a Lithium Acetylide to a Ketone:  Solution Structures and Relative Reactivities of Mixed Aggregates Underlying the High Enantioselectivities

Andrew S. Thompson, Edward G. Corley, Martha Huntington et al. · Journal of the American Chemical Society · 1998 · 162 citations

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Use of an ephedrine alkoxide to mediate enantioselective addition of an acetylide to a prochiral ketone: asymmetric synthesis of the reverse transcriptase inhibitor L-743,726

Andrew S. Thompson, Edward G. Corley, Martha Huntington et al. · Tetrahedron Letters · 1995 · 131 citations

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Derivatives of (+)-Limonene. III. A Stereospecific Synthesis of cis- and trans-Δ<sup>8(9)</sup>-p-Menthene 1,2-Epoxides<sup>1</sup>

William F. Newhall · The Journal of Organic Chemistry · 1964 · 33 citations

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