A short enantioselective synthesis of N-boc-(2R,3R)-3-methyl-3-hydroxypipecolic acid from geraniol

被引：6

作者：

Noe, Mark C. ^{[1
]}

Hawkins, Joel M. ^{[1
]}

Snow, Sheri L. ^{[1
]}

Wolf-Gouveia, Lilli ^{[1
]}

机构：

[1] Pfizer Global Res & Dev, Groton, CT 06340 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 08期

关键词：

D O I：

10.1021/jo800080t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric synthesis of (2R,3R)-3-methyl-3-hydroxypipecolic acid, a key intermediate in the synthesis of dual MMP-13/aggrecanase inhibitors, is described. The title compound is prepared in seven steps with an overall yield of 41% starting from geraniol. Key steps in the synthesis include Sharpless asymmetric epoxidation, which establishes the chiral centers, and a one-pot oxidative olefin cleavage/reductive amination sequence that closes the piperidine ring.

引用

页码：3295 / 3298

页数：4

共 50 条

[21] ASYMMETRIC-SYNTHESIS OF THE N-TERMINAL COMPONENT OF MICROGININ - (2S,3R)-3-AMINO-2-HYDROXYDECANOIC ACID, ITS (2R,3R)-EPIMER AND (3R)-3-AMINODECANOIC ACID
BUNNAGE, ME
BURKE, AJ
DAVIES, SG
GOODWIN, CJ
TETRAHEDRON-ASYMMETRY, 1995, 6 (01) : 165 - 176
[22] (2R,3R)-3-O-Benzoyl-N-benzyltartramide
Madura, Izabela D.
Zachara, Janusz
Bernas, Urszula
Hajmowicz, Halina
Synoradzki, Ludwik
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O1891 - +
[23] Enantioselective synthesis of (2R,3R)- and (2S,3S)-2-[(3-chlorophenyl)-(2-methoxyphenoxy)methyl]morpholine
Harding, WW
Hodge, M
Wang, ZX
Woolverton, WL
Parrish, D
Deschamps, JR
Prisinzano, TE
TETRAHEDRON-ASYMMETRY, 2005, 16 (13) : 2249 - 2256
[24] An Efficient Synthesis of Enantiopure (2R,3R)-β-Methoxytyrosine
Fan, Shi-Ming
Tian, Xia
Yang, Yi-Hua
Jin, Long Yi
Liu, Shou-xin
SYNLETT, 2015, 26 (18) : 2553 - 2556
[25] Asymmetric synthesis of (2R,3S)-3-hydroxypipecolic acid δ-lactam derivatives
Koulocheri, SD
Magiatis, P
Skaltsounis, AL
Haroutounian, SA
TETRAHEDRON, 2002, 58 (33) : 6665 - 6671
[26] DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF (1R,3R)-CARONALDEHYDE ACID METHYL-ESTER AND (1R,3R)-CHRYSANTHEMIC ACID METHYL-ESTER FROM (R)-GLYCERINALDEHYDE ACETONIDE
MULZER, J
KAPPERT, M
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1983, 22 (01): : 63 - 64
[27] Synthesis of (2R,3R)-N -Fmoc-3-TBDMSilyloxy-aspartic acid-allyl ester.
Boyaud, F.
Inguimbert, N.
JOURNAL OF PEPTIDE SCIENCE, 2012, 18 : S187 - S187
[28] (R)-histidinium (2R,3R)-tartrate
Johnson, MN
Feeder, N
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2004, 60 : O1476 - O1477
[29] Pyridinium (2R,3R)-tartrate
Suresh, J.
Krishnakumar, R. V.
Rajagopal, K.
Natarajan, S.
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2006, 62 : O3220 - O3222
[30] Syntheses of (-)-(2R,3R,6S)-irnigaine and (+)-(2R,3R,6S)-N-methylirnigaine
Pahl, A
Wartchow, R
Meyer, HH
TETRAHEDRON LETTERS, 1998, 39 (15) : 2095 - 2096

← 1 2 3 4 5 →