An efficient chiral moderator prepared from inexpensive (+)3-carene: Synthesis of the HIV-1 non-nucleoside reverse transcriptase inhibitor DPC 963

Authors
Kauffman, GS Harris, GD Dorow, RL Stone, BRP Parsons, RL Pesti, JA Magnus, NA Fortunak, JM Confalone, PN Nugent, WA
Citation
Gs. Kauffman et al., An efficient chiral moderator prepared from inexpensive (+)3-carene: Synthesis of the HIV-1 non-nucleoside reverse transcriptase inhibitor DPC 963, ORG LETT, 2(20), 2000, pp. 3119-3121
Citations number
20
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
20
Year of publication
2000
Pages
3119 - 3121
Database
ISI
SICI code
1523-7060(20001005)2:20<3119:AECMPF>2.0.ZU;2-H
Abstract
[GRAPHICS] The beta-amino alcohol 4 beta-morpholinocaran-3 alpha-ol is prepared by add ition of morpholine to alpha-3,4-epoxycarane utilizing anhydrous magnesium bromide as Lewis acid promoter. The enantiopure amino alcohol is uniquely e ffective as a chiral moderator for the addition of lithium cyclopropylacety lide to an unprotected N-acylketimine. This reaction provides an efficient route to the second generation NNRTI drug candidate DPC 963.