A Flexible Approach to Grandisine Alkaloids: Total Synthesis of Grandisines B, D, and F

被引：28

作者：

Kurasaki, Haruaki ^{[2
]}

Okamoto, Iwao ^{[1
]}

Morita, Nobuyoshi ^{[1
]}

Tamura, Osamu ^{[1
]}

机构：

[1] Showa Pharmaceut Univ, Tokyo 1948543, Japan

[2] Kyorin Pharmaceut Co Ltd, Exploratory Res Labs, Nogi, Tochigi 3290114, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 46期

关键词：

alkaloids; natural products; nitrogen heterocycles; total synthesis; RECEPTOR-BINDING AFFINITY; INDOLIZIDINE ALKALOIDS; ABSOLUTE-CONFIGURATION; ASYMMETRIC-SYNTHESIS; ACYLIMINIUM IONS; IMINIUM ION; LEAVES; ACID; CYCLIZATIONS; VINYLSILANES;

D O I：

10.1002/chem.200901843

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This article describes in detail the first total synthesis of grandisine alkaloids, grandisines B, D, and F, which show affinity for the human delta-opioid receptor. The key steps in this synthesis are construction of the isoquinuclidinone moiety of 2 by intramolecular imine formation and the tetracyclic ring system of 4 by stereoselective ring closure of the enolate of amine 8 generated by 1,4-addition of ammonia to 9. Synthesis of key intermediate 9 featured a highly stereoselective Bronsted acid mediated Morita-Baylis-Hillman (MBH) reaction via the N-acyl iminium ion.

引用

页码：12754 / 12763

页数：10

共 43 条

[11] Indolizidine alkaloids with δ-opioid receptor binding affinity from the leaves of Elaeocarpus fuscoides [J].

Katavic, Peter L. ;

Venables, Debra A. ;

Rali, Topul ;

Carroll, Anthony R. .

JOURNAL OF NATURAL PRODUCTS, 2007, 70 (05) :872-875

[12] Habbemines a and b, pyrrolidine alkaloids with human δ-opioid receptor binding affinity from the leaves of Elaeocarpus habbemensis [J].

Katavic, Peter L. ;

Venables, Debra A. ;

Rali, Topul ;

Carroll, Anthony R. .

JOURNAL OF NATURAL PRODUCTS, 2007, 70 (05) :866-868

[13] Grandisines C-G, indolizidine alkaloids from the Australian rainforest tree Elaeocarpus grandis [J].

Katavic, Peter L. ;

Venables, Debra A. ;

Forster, Paul I. ;

Guymer, Gordon ;

Carroll, Anthony R. .

JOURNAL OF NATURAL PRODUCTS, 2006, 69 (09) :1295-1299

[14] ABSOLUTE CONFIGURATION OF PULEGONE OXIDE AND PIPERITENONE DIOXIDE [J].

KATSUHARA, J .

JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (03) :797-+

[15] Perchloric acid impregnated on silica gel (HClO4/SiO2):: A versatile catalyst for Michael addition of thiols to the electron-deficient alkenes [J].

Khan, Abu T. ;

Ghosh, Subrata ;

Choudhury, Lokman H. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (09) :2226-2231

[16] SYNTHESIS AND ABSOLUTE-CONFIGURATION OF THE ARISTOTELIA ALKALOID PEDUNCULARINE [J].

KLAVER, WJ ;

HIEMSTRA, H ;

SPECKAMP, WN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) :2588-2595

[17] The intramolecular tandem Michael/Mannich-type reaction of α,β-unsaturated carbonyl compounds with acyliminium ions provides access to chiral indolizidines [J].

Koseki, Yuji ;

Fujino, Koji ;

Takeshita, Ai ;

Sato, Hiroto ;

Nagasaka, Tatsuo .

TETRAHEDRON-ASYMMETRY, 2007, 18 (13) :1533-1539

[18] Total Synthesis of Grandisine D [J].

Kurasaki, Haruaki ;

Okamoto, Iwao ;

Morita, Nobuyoshi ;

Tamura, Osamu .

ORGANIC LETTERS, 2009, 11 (05) :1179-1181

[19] Asymmetric synthesis of furo[3,2-i]indolizines from L-malic acid [J].

Lee, YS ;

Lee, JY ;

Kim, DW ;

Park, HK .

TETRAHEDRON, 1999, 55 (15) :4631-4636

[20] ASYMMETRIC-SYNTHESIS OF BOTH ENANTIOMERS OF PYRROLIDINOISOQUINOLINE DERIVATIVES FROM L-MALIC ACID AND L-TARTARIC ACID [J].

LEE, YS ;

KANG, DW ;

LEE, SJ ;

PARK, H .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22) :7149-7152

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