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

被引：183

作者：

Kauffman, GS ^{[1
]}

Harris, GD ^{[1
]}

Dorow, RL ^{[1
]}

Stone, BRP ^{[1
]}

Parsons, RL ^{[1
]}

Pesti, JA ^{[1
]}

Magnus, NA ^{[1
]}

Fortunak, JM ^{[1
]}

Confalone, PN ^{[1
]}

Nugent, WA ^{[1
]}

机构：

[1] Dupont Merck Pharmaceut Co, Chem Proc R&D, Chambers Works, Deepwater, NJ 08023 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 20期

关键词：

D O I：

10.1021/ol006321x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] 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.

引用

页码：3119 / 3121

页数：3

共 21 条

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