Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine

被引：17

作者：

Compostella, F

Franchini, L

Giovenzana, GB

Panza, L

Prosperi, D

Ronchetti, F

机构：

[1] Univ Piemonte Orientale, Dipartimento Sci Chim Alimentari Farmaceut & Farm, I-28100 Novara, Italy

[2] Univ Milan, Dipartimento Chim & Biochim Med, I-20133 Milan, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 08期

关键词：

D O I：

10.1016/S0957-4166(02)00201-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The synthesis of 3-O-benzoyl azidosphingosine 1 through a stereoconvergent approach is described. Nucleophilic addition of the Grignard reagent of 1-pentadecyne to cyclohexylidene-D-glyceraldehyde results in a mixture of diastereoisomeric propargylic alcohols. Subsequent enzymatic separation of these diastereoisomers, mediated by lipase from Candida antarctica, Mitsunobu inversion on the wrong diastereoisomer and extremely efficient introduction of azide using a chloromesylate leaving group affords the title compound in 30% overall yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：867 / 872

页数：6

共 18 条

[1] Formal total synthesis of nikkomycin B based on a lipase-catalysed hydrolysis of an acetate possessing two stereogenic centers
Akita, H
Chen, CY
Kato, K
[J]. TETRAHEDRON, 1998, 54 (37) : 11011 - 11026
[2] Chemoenzymatic synthesis of glycosylated enantiomerically pure 4-pentene 1,2- and 1,3-diol derivatives
Bien, F
Ziegler, T
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (05) : 781 - 790
[3] ENANTIOSELECTIVE ESTERIFICATIONS OF UNSATURATED ALCOHOLS MEDIATED BY A LIPASE PREPARED FROM PSEUDOMONAS SP
BURGESS, K
JENNINGS, LD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) : 6129 - 6139
[4] (R)-2,3-O-CYCLOHEXYLIDENEGLYCERALDEHYDE, A VERSATILE INTERMEDIATE FOR ASYMMETRIC-SYNTHESIS OF CHIRAL ALCOHOL
CHATTOPADHYAY, A
MAMDAPUR, VR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (03) : 585 - 587
[5] (R)-2,3-O-cyclohexylideneglyceraldehyde, a versatile intermediate for asymmetric synthesis of homoallyl and homopropargyl alcohols in aqueous medium
Chattopadhyay, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) : 6104 - 6107
[6] H-1-NMR ACETYL METHYL RESONANCES OF PERACETYLATED LILIOSIDE-B - A TOOL FOR THE STEREOCHEMICAL IDENTIFICATION OF ITS PARTIALLY ACETYLATED DERIVATIVES
COLOMBO, D
ALBINI, FM
SCALA, A
TAINO, IM
TOMA, L
[J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (10) : 1993 - 1998
[7] Synthesis of an orthogonally protected D-(+)-erythro-sphingosine
Gargano, JM
Lees, WJ
[J]. TETRAHEDRON LETTERS, 2001, 42 (34) : 5845 - 5847
[8] STUDIES ON THE THIOGLYCOSIDES OF N-ACETYLNEURAMINIC ACID .6. SYNTHESIS OF GANGLIOSIDE GM4 ANALOGS
ITO, Y
KISO, M
HASEGAWA, A
[J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1989, 8 (02) : 285 - 294
[9] Application of a stereospecific intramolecular allenylsilane imino ene reaction to enantioselective total synthesis of the 5,11-methanomorphanthridine class of Amaryllidaceae alkaloids
Jin, J
Weinreb, SM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (25) : 5773 - 5784
[10] Kumar P, 1998, SYNTHESIS-STUTTGART, P33

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