A short and efficient synthesis of 2R,3R,4R-3,4-dihydroxyproline, 1,4-dideoxy-1,4-imino-L-xylitol, 2R,3R,4R,5S-3,4,5-trihydroxypipecolic acid, and 1,5-dideoxy-1,5-imino-L-iditol

被引：0

作者：

Lee, BW ^{[1
]}

Jeong, IY ^{[1
]}

Yang, MS ^{[1
]}

Choi, SU ^{[1
]}

Park, KH ^{[1
]}

机构：

[1] Gyeongsang Natl Univ, Dept Agr Chem, Chinju 660701, South Korea

来源：

SYNTHESIS-STUTTGART | 2000年 / 09期

关键词：

carbohydrates; iodine; amino acids; one-pot cyclization; azasugars; protecting group;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The syntheses of pyrrolidine alkaloids (-)-1 and (+)-3 were accomplished in 47% and 60% overall yield from 2-azido-2-deoxy-L-idonate 5, while piperidine alkaloids (-)-2 and (+)-4 were obtained in 51% acid 53% overall yield from the same starting material. Key step includes iodine promoted one-pot cyclization, and selective deprotection of isopropylidene and 9-phenylfluoren-9-yl (Pf) group.

引用

页码：1305 / 1309

页数：5

共 50 条

[1] A STEREOSPECIFIC SYNTHESIS OF (+)-2-EPIDEOXYMANNOJIRIMYCIN AND (2R,3R,4R,5R)-3,4,5-TRIHYDROXYPIPECOLIC ACID
PARK, KH
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1995, 16 (10) : 985 - 988
[2] THE SYNTHESIS OF POLYHYDROXYLATED AMINO-ACIDS FROM GLUCURONOLACTONE - ENANTIOSPECIFIC SYNTHESES OF 2S,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2R,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID AND 2R,3R,4R-DIHYDROXYPROLINE
BASHYAL, BP
CHOW, HF
FELLOWS, LE
FLEET, GWJ
TETRAHEDRON, 1987, 43 (02) : 415 - 422
[3] SYNTHESIS OF HOMOCHIRAL BETA-HYDROXY-ALPHA-AMINO-ACIDS [(2S,3R,4R)-3,4-DIHYDROXYPROLINE AND (2S,3R,4R)-3,4-DIHYDROXYPIPECOLIC ACID] AND OF 1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL [DAB1] AND FAGOMINE [1,5-IMINO-1,2,5-TRIDEOXY-D-ARABINO-HEXITOL]
FLEET, GWJ
WITTY, DR
TETRAHEDRON-ASYMMETRY, 1990, 1 (02) : 119 - 136
[4] Experimental and Calculated Vibrational Circular Dichroism Spectra of an Iminosugar Molecule: (2R, 3R, 4R) 1,4-dideoxy-1,4-imino-D-arabinitol Hydrochloride
Teodorescu, Florina
Man, Isabela Costinela
Stavarache, Carmen
Naubron, Jean-Valere
Hirtopeanu, Anca
REVISTA DE CHIMIE, 2013, 64 (04): : 351 - 354
[5] Stereoselective synthesis of 1,4-dideoxy-1,4-imino-D-allitol and formal synthesis of (2S,3R,4S)-3,4-dihydroxyproline
Madhan, A
Rao, BV
TETRAHEDRON LETTERS, 2003, 44 (30) : 5641 - 5643
[6] Asymmetric Synthesis of D-Proline, D-Pipecolic Acid, (2R,3S,4R)-3,4-Dihydroxyproline, and 1,4-Dideoxy-1,4-imino-D-talitol from a Common Precursor
Chattopadhyay, Shital K.
Mukherjee, Jyoti Prasad
SYNTHESIS-STUTTGART, 2014, 46 (18): : 2481 - 2488
[7] 2S,3R,4R,5S)-3,4,5-trihydroxypipecolic acid dihydrate [(2S,3R,4R,5S)-3,4,5-tri-hydroxypiperidine-2-carboxylic acid dihydrate]
Booth, Kathrine V.
Jenkinson, Sarah F.
Watkin, David J.
Sharp, Hazel
Jones, Paul Wyn
Nash, Robert J.
Fleet, George W. J.
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O3783 - U2810
[8] SIMPLE SYNTHESIS OF (-)-DEOXYMANNOJIRIMYCIN AND (2S,3R,4R,5R)-3,4,5-TRIHYDROXYPIPECOLIC ACID VIA REGIOSELECTIVE HYDROLYSIS
PARK, KH
YOON, YJ
LEE, SG
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (18): : 2621 - 2623
[9] A PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND OF (2S, 3R, 4R, 5R)-3,4,5-TRIHYDROXYPIPECOLIC ACID FROM D-GLUCOSE
FLEET, GWJ
RAMSDEN, NG
WITTY, DR
TETRAHEDRON, 1989, 45 (01) : 327 - 336
[10] A SHORT DIASTEREOSELECTIVE SYNTHESIS OF THE NATURAL (2R, 3R, 4R)-2-HYDROXYMETHYL-3,4-DIHYDROXYPYRROLIDINE
GRIFFARTBRUNET, D
LANGLOIS, N
TETRAHEDRON LETTERS, 1994, 35 (18) : 2889 - 2890

← 1 2 3 4 5 →