The stereocontrolled synthesis of orthogonally protected (R)-α-methyltryptophan

被引：5

作者：

Goodman, M ^{[1
]}

Zhang, JF ^{[1
]}

Gantzel, P ^{[1
]}

Benedetti, E ^{[1
]}

机构：

[1] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 52期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(98)02302-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An expedient and highly stereocontrolled route to (R)-alpha-methyltryptophan and its orthogonally protected analogs has been developed via a four-step conversion from L-alanine in good overall yields. The stereochemistry of the products is confirmed by X-ray diffraction analysis, NMR spectroscopy and optical rotations. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：9589 / 9592

页数：4

共 50 条

[1] Stereocontrolled synthesis of orthogonally protected 2-substituted 4-aminopiperidines
Badorrey, Ramon
Portana, Elsa
Diaz-de-Villegas, Maria D.
Galvez, Jose A.
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (14) : 2912 - 2918
[2] Synthesis of orthogonally protected τ-histidinoalanine
Taylor, Carol M.
Batton, Chyree S.
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
[3] Synthesis of Orthogonally Protected Labionin
Lo Presti, Eliana
Volonterio, Alessandro
Sani, Monica
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (05): : 4313 - 4319
[4] Synthesis of orthogonally protected lanthionines
Mustapa, MFM
Harris, R
Bulic-Subanovic, N
Elliott, SL
Bregant, S
Groussier, MFA
Mould, J
Schultz, D
Chubb, NAL
Gaffney, PRJ
Driscoll, PC
Tabor, AB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (21): : 8185 - 8192
[5] An efficient synthesis of orthogonally protected spermidine
Amssoms, K
Augustyns, K
Yamani, A
Zhang, M
Haemers, A
[J]. SYNTHETIC COMMUNICATIONS, 2002, 32 (03) : 319 - 328
[6] Synthesis of orthogonally protected and functionalized bacillosamines
van Mechelen, Jeanine
Voorneveld, Jim
Overkleeft, Hermen S.
Filippov, Dmitri V.
van der Marel, Gijsbert A.
Codee, Jeroen D. C.
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (15) : 2834 - 2837
[7] Stereoselective synthesis of orthogonally protected α-methylnorlanthionine
Avenoza, Alberto
Busto, Jesuus H.
Jimenez-Oses, Gonzalo
Peregrina, Jesus M.
[J]. ORGANIC LETTERS, 2006, 8 (13) : 2855 - 2858
[8] The stereospecific synthesis of 'orthogonally' protected lanthionines
Swali, V
Matteucci, M
Elliot, R
Bradley, M
[J]. TETRAHEDRON, 2002, 58 (44) : 9101 - 9109
[9] Optimized synthesis of an orthogonally protected glucosamine
Hernández-Torres, JM
Liew, ST
Achkar, J
Wei, A
[J]. SYNTHESIS-STUTTGART, 2002, (04): : 487 - 490
[10] Efficient enantioselective synthesis of orthogonally protected (R)-α-alkylserines compatible with the solid phase peptide synthesis
Vassiliou, Stamatia
Yiotakis, Athanasios
Magriotis, Plato A.
[J]. TETRAHEDRON LETTERS, 2006, 47 (41) : 7339 - 7341

← 1 2 3 4 5 →