Cycloaddition of an enantiopure cyclic nitrone to maleate: Straightforward synthesis of the necine base (-)-hastanecine

被引：0

作者：

Goti, A

Fedi, V

Nannelli, L

DeSarlo, F

Brandi, A

机构：

来源：

SYNLETT | 1997年 / 05期

关键词：

pyrrolizidine alkaloids; (-)-hastanecine; necine bases; Mitsunobu reaction; enantiomerically pure cyclic nitrones;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A formal synthesis of the necine base (-)-hastanecine, subunit of the pyrrolizidine alkaloids hastacine and punctanecine, is reported. The key intermediate 7 is synthesized in five steps from dimesylate 11, derived from L-malic acid, in 28.3% overall yield. The correct absolute stereochemistry at C7 in the target compound is attained by means of a Mitsunobu reaction on dimesylate 11. The desired stereochemistry at the remaining stereogenic centres (C1 and C7a) derives from a highly preferential exo-anti approach in the key cycloaddition of nitrone 9 (obtained with complete regiocontrol) to dimethyl maleate.

引用

页码：577 / &

页数：4

共 25 条

[11] Asymmetric [3+2] cycloaddition reaction of a chiral cyclic nitrone for the synthesis of new tropane alkaloids
Esteban, Alberto
Izquierdo, Ignacio
Garcia, Nieves
Sexmero, Maria J.
Garrido, Narciso M.
Marcos, Isidro S.
Sanz, Francisca
Jambrina, Pablo G.
Ortega, Pablo
Diez, David
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[12] Synthesis and asymmetric [3+2] cycloaddition reactions of chiral cyclic nitrone: A novel system providing maximal facial bias for both nitrone and dipolarophile
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Tajima, Y
Fukui, M
Saito, S
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (16): : 1863 - 1864
[13] Highly Diastereoselective 1,3-Dipolar Cycloaddition of a D-Galactose-Derived Nitrone with Dimethyl Maleate: Synthesis of Polyhydroxylated Perhydroazaazulenes
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Jadhav, Vrushali H.
Puranik, Vedavati G.
Dhavale, Dilip D.
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[14] Synthesis of casuarine-related derivatives via 1,3-dipolar cycloaddition between a cyclic nitrone and an unsaturated γ-lactone
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[15] Synthesis of the Potential Mannosidase Inhibitor via 1,3-Dipolar Cycloaddition Involving Cyclic Nitrone and Unsaturated Chiral γ-Lactone
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Pasniczek, K.
Jurczak, M.
Solecka, J.
Chmielewski, M.
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[16] CYCLOADDITION REACTIONS OF CARBOHYDRATE-DERIVATIVES .4. SYNTHESIS OF A TETRAHYDROXYINDOLIZIDINE THROUGH A CYCLIC NITRONE PREPARED FROM D-XYLOSE
HERCZEGH, P
KOVACS, I
SZILAGYI, L
VARGA, T
DINYA, Z
SZTARICSKAI, F
TETRAHEDRON LETTERS, 1993, 34 (07) : 1211 - 1214
[17] Formal Synthesis of Sarain A: Intramolecular Cycloaddition of an Eight-Membered Cyclic Nitrone to Construct the 2-Azabicyclo-[3.3.1]nonane Framework
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Ukegawa, Tomoya
Yokoshima, Satoshi
Fukuyama, Tohru
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[18] Synthesis of Constrained C-Glycosyl Amino Acid Derivatives Involving 1,3-Dipolar Cycloaddition of Cyclic Nitrone as Key Step
Rouzier, Florian
Sille, Rosanne
Montiege, Ophelie
Tessier, Arnaud
Pipelier, Muriel
Dujardin, Gilles
Martel, Arnaud
Nourry, Arnaud
Guillarme, Stephane
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[19] Straightforward access to enantiomerically pure, highly functionalized pyrrolizidines by cycloaddition of maleic acid esters to pyrroline N-oxides derived from tartaric, malic and aspartic acids -: Synthesis of (-)-hastanecine, 7-epi-croalbinecine and (-)-croalbinecine
Goti, A
Cicchi, S
Cacciarini, M
Cardona, F
Fedi, V
Brandi, A
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 2000 (21) : 3633 - 3645
[20] A 5-MEMBERED ENANTIOPURE CYCLIC NITRONE FROM MALIC-ACID BY REGIOSELECTIVE OXIDATION OF CYCLIC HYDROXYLAMINE - SYNTHESIS OF (1S,7S,8AR)-OCTAHYDRO-1,7-DIHYDROXYINDOLIZINE
CICCHI, S
GOTI, A
BRANDI, A
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15): : 4743 - 4748

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