Full stereochemical understanding in a new (2R,3R,4R)-4-hydroxyisoleucine synthesis

被引：2

作者：

Rolland, M

Kassem, T

Rolland, V

Martinez, J

机构：

[1] Univ Montpellier I, Lab Aminoacides Peptides & Prot, Fac Pharm, CNRS,UMR 5810, F-34060 Montpellier 2, France

[2] Univ Montpellier 2, Lab Aminoacides Peptides & Prot, Fac Pharm, CNRS,UMR 5810, F-34060 Montpellier 2, France

来源：

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY | 2001年 / 57卷 / 12期

关键词：

D O I：

10.1107/S0108270101014597

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We present the crystal and molecular structures of 2,3,6,7,8,8a-hexahydro-6,8-methano-7,7,8a-trimethyl-3-(1-methyl-2-oxo- propylidene)-5H-1,4-benzoxazin-2-one, C16H21NO3, (III), and 2,3,6,7,8,8a-hexahydro-3-(2-hydroxy-1-methylpropyl)-6,8-methano-7,7,8a-trimethyl-5H-1,4-benzoxazin-2-one, C16H25NO3, (V). These compounds are two of the four key intermediates in our synthetic route to (2R,3R,4R)-4-hydroxyisoleucine. The two structures provide a full understanding of the stereochemistry in successive steps. This synthesis was based on a new optically pure chiral oxazinone auxiliary derived from (1R,2R,5R)-2-hydroxypinan-3-one.

引用

页码：1415 / 1417

页数：3

共 50 条

[1] Practical, efficient, stereoselective, formal synthesis of (2R,3R,4R)-3-hydroxy-4-methylproline
Raghavan, S
Reddy, SR
TETRAHEDRON LETTERS, 2003, 44 (40) : 7459 - 7462
[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] 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
[4] (+)-(3S,4R)-Norcisapride hydrogen (2R,3R)-tartrate monohydrate
Peeters, OM
Blaton, NM
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2002, 58 : O1169 - O1171
[5] Concise Synthesis of (2R,4R)-Monatin
Amino, Yusuke
CHEMICAL & PHARMACEUTICAL BULLETIN, 2016, 64 (08) : 1242 - 1247
[6] The synthesis of C2 symmetry diesters of (3R,4R)-TTFOL through a green and stereoselective (2R,3R)-TADDOL rearrangement
Costantino, Andrea R.
Montiel Schneider, Maria Gabriela
Galdamez, Antonio
Ocampo, Romina A.
Mandolesi, Sandra D.
Koll, Liliana C.
TETRAHEDRON-ASYMMETRY, 2015, 26 (23) : 1341 - 1347
[7] Total synthesis of the acetyl derivatives of lyxo-(2R,3R,4R)-phytosphingosine and (-)-jaspine B
Rao, Ganipisetti Srinivas
Chandrasekhar, Bandari
Rao, Batchu Venkateswara
TETRAHEDRON-ASYMMETRY, 2012, 23 (08) : 564 - 569
[8] An Organocatalyzed Enantioselective Synthesis of (2S,3R,4S)-4-Hydroxyisoleucine and Its Stereoisomers
Kumaraswamy, Gullapalli
Jayaprakash, Neerasa
Sridhar, Balasubramanian
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (08): : 2745 - 2747
[9] Chemoenzymatic synthesis of (2R,3R,4R)-dehydroxymethylepoxyquinomicin (DHMEQ), a new activator of antioxidant transcription factor Nrf2
Niitsu, Yukihiro
Hakamata, Masatoshi
Goto, Yuko
Higashi, Toshinori
Shoji, Mitsuru
Sugai, Takeshi
Umezawa, Kazuo
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (12) : 4635 - 4641
[10] Synthesis of hydantoin analogues of (2S, 3R, 4S)-4-hydroxyisoleucine with insulinotropic properties
Sergent, Didier
Wang, Qian
Sasaki, N. Andre
Ouazzani, Jamal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (15) : 4332 - 4335

← 1 2 3 4 5 →