Stereoselective synthesis of (-)-cytoxazone

被引：35

作者：

Carda, M ^{[1
]}

González, F

Sánchez, R

Marco, JA

机构：

[1] Univ Jaume 1, Dept Quim Organ & Inorgan, E-12080 Castellon de La Plana, Spain

[2] Univ Valencia, Dept Quim Organ, E-46100 Valencia, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 09期

关键词：

D O I：

10.1016/S0957-4166(02)00227-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The stereoselective synthesis of the cytokine modulator (-)-cytoxazone in enantiopure form is described. Key steps of the process are a syn-stereoselective aldol addition of a chiral ketone mediated by chlorodicyclohexylborane, and a Curtius rearrangement. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1005 / 1010

页数：6

共 26 条

[11] LIPSHUTZ BH, 1992, ORG REACTIONS, V41, P135, DOI [DOI 10.1002/0471264180.0R041.02, 10.1002/0471264180.or041.02]
[12] Stereoselective synthesis of (-)-cytoxazone
Madhan, A
Kumar, AR
Rao, BV
[J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (14) : 2009 - 2011
[13] Dibutyltin oxide catalyzed selective sulfonylation of α-chelatable primary alcohols
Martinelli, MJ
Nayyar, NK
Moher, ED
Dhokte, UP
Pawlak, JM
Vaidyanathan, R
[J]. ORGANIC LETTERS, 1999, 1 (03) : 447 - 450
[14] Miyata O, 1999, SYNLETT, P1915
[15] PHOSPHORUS IN ORGANIC SYNTHESIS .7. DIPHENYL PHOSPHORAZIDATE (DPPA) - NEW CONVENIENT REAGENT FOR A MODIFIED CURTIUS REACTION
NINOMIYA, K
SHIOIRI, T
YAMADA, S
[J]. TETRAHEDRON, 1974, 30 (14) : 2151 - 2157
[16] Diastereoselective and convergent synthesis of both 11'-epimers of (-)-(2R,3R,6S)-carnavaline
Pahl, A
Oetting, J
Holzkamp, J
Meyer, HH
[J]. TETRAHEDRON, 1997, 53 (21) : 7255 - 7266
[17] Efficient synthesis of the γ-amino-β-hydroxy acid subunit of hapalosin
Pais, GCG
Maier, ME
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) : 4551 - 4554
[18] Synthetic applications of the cyclic iminocarbonate rearrangement:: enantioselective syntheses of chloramphenicol and 4-epi-cytoxazone
Park, JN
Ko, SY
Koh, HY
[J]. TETRAHEDRON LETTERS, 2000, 41 (29) : 5553 - 5556
[19] Concise enantio- and diastereoselective synthesis of α-hydroxy-α-methyl-β-amino acids
Roers, R
Verdine, GL
[J]. TETRAHEDRON LETTERS, 2001, 42 (21) : 3563 - 3565
[20] Design and synthesis of dipeptidyl α′,β′-epoxy ketones, potent irreversible inhibitors of the cysteine protease cruzain
Roush, WR
González, FV
McKerrow, JH
Hansell, E
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (19) : 2809 - 2812

← 1 2 3 →