A concise synthesis of the HIV-protease inhibitor nelfinavir via an unusual tetrahydrofuran rearrangement

被引：26

作者：

Zook, SE ^{[1
]}

Busse, JK ^{[1
]}

Borer, BC ^{[1
]}

机构：

[1] Agouron Pharmaceut Inc, Chem Dev, San Diego, CA 92121 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 36期

关键词：

D O I：

10.1016/S0040-4039(00)01231-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of nelfinavir 1 was developed. The synthesis features an unusual rearrangement of a 3-amidotetrahydrofuran into a functionalized oxazoline. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：7017 / 7021

页数：5

共 5 条

[1] HIV-protease inhibitors
Flexner, C
[J]. NEW ENGLAND JOURNAL OF MEDICINE, 1998, 338 (18) : 1281 - 1292
[2] A practical synthesis of nelfinavir, an HIV-protease inhibitor, using a novel chiral C4 building block:: (5R,6S)-2,2-dimethyl-5-hydroxy-1,3-dioxepan-6-ylammonium acetate
Inaba, T
Birchler, AG
Yamada, Y
Sagawa, S
Yokota, K
Ando, K
Uchida, I
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) : 7582 - 7583
[3] Practical synthesis of enantiopure cyclic 1,2-amino alcohols via catalytic asymmetric ring opening of meso epoxides
Schaus, SE
Larrow, JF
Jacobsen, EN
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) : 4197 - 4199
[4] A REMARKABLE BASE-INDUCED REARRANGEMENT OF HYDROXY OXAZOLINES TO AMIDO TETRAHYDROFURANS
WILSON, KJ
SABAT, M
MCGARVEY, GJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (23) : 6180 - 6181
[5] YAMAZAKI H, 1992, CHEM PHARM BULL, V40, P102

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