Stereocontrolled Total Synthesis of Antimalarial (+)-Axisonitrile-3

被引：16

作者：

Tamura, Keiji ^{[1
]}

Nakazaki, Atsuo ^{[1
]}

Kobayashi, Susumu ^{[1
]}

机构：

[1] Tokyo Univ Sci RIKADAI, Fac Pharmaceut Sci, Noda, Chiba 2788510, Japan

来源：

SYNLETT | 2009年 / 15期

关键词：

antimalarial activity; (+)-axisonitrile-3; Claisen rearrangement; O-methyl oxime; total synthesis; SPONGE ACANTHELLA-CAVERNOSA; (+/-)-WELWITINDOLINONE-A ISONITRILE; MARINE; SESQUITERPENES;

D O I：

10.1055/s-0029-1217826

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Here we describe the total synthesis of the antimalarial sesquiterpene, (+)-axisonitrile-3. Three key features of this synthesis are: (i) non-Evans syn-aldol reaction of an isovaleric acid derivative bearing a chiral oxazolidinethione and crotonaldehyde with high diastereoselectivity, (ii) Claisen rearrangement of alkenyl dihydropyran affording spiro[4.5]decane with requisite functionalities, and (iii) highly stereoselective reduction in the sterically congested O-methyl oxime system.

引用

页码：2449 / 2452

页数：4

共 14 条

[1] ANTIMALARIAL ACTIVITY OF SESQUITERPENES FROM THE MARINE SPONGE ACANTHELLA-KLETHRA
ANGERHOFER, CK
PEZZUTO, JM
KONIG, GM
WRIGHT, AD
STICHER, O
[J]. JOURNAL OF NATURAL PRODUCTS, 1992, 55 (12): : 1787 - 1789
[2] TOTAL SYNTHESIS OF (-)-AXISONITRILE-3 - APPLICATION OF REDUCTIVE RING-OPENING OF VINYLCYCLOPROPANES
CAINE, D
DEUTSCH, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (25) : 8030 - 8031
[3] Asymmetric aldol additions with titanium enolates of acyloxazolidinethiones: Dependence of selectivity on amine base and Lewis acid stoichiometry
Crimmins, MT
King, BW
Tabet, EA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (33) : 7883 - 7884
[4] AXISONITRILE-3, AXISOTHIOCYANATE-3 AND AXAMIDE-3 - SESQUITERPENES WITH A NOVEL SPIRO[4,5]DECANE SKELETON FROM SPONGE AXINELLA-CANNABINA
DIBLASIO, B
FATTORUSSO, E
MAGNO, S
MAYOL, L
PEDONE, C
SANTACROCE, C
SICA, D
[J]. TETRAHEDRON, 1976, 32 (04) : 473 - 478
[5] Marine isocyanides and related natural products structure, biosynthesis and ecology
Garson, MJ
Simpson, JS
[J]. NATURAL PRODUCT REPORTS, 2004, 21 (01) : 164 - 179
[6] Terpenoids with antifouling activity against barnacle larvae from the marine sponge Acanthella cavernosa
Hirota, H
Tomono, Y
Fusetani, N
[J]. TETRAHEDRON, 1996, 52 (07) : 2359 - 2368
[7] A comparison of sesquiterpene scaffolds across different populations of the tropical marine sponge Acanthella cavernosa
Jumaryatno, Pinus
Stapleton, Bronwin L.
Hooper, John N. A.
Brecknell, Douglas J.
Blanchfield, Joanne T.
Garson, Mary J.
[J]. JOURNAL OF NATURAL PRODUCTS, 2007, 70 (11): : 1725 - 1730
[8] Ligand-based virtual screening and in silico design of new antimalarial compounds using nonstochastic and stochastic total and atom-type quadratic maps
Marrero-Ponce, Y
Iyarreta-Veitía, M
Montero-Torres, A
Romero-Zaldivar, C
Brandt, CA
Avila, PE
Kirchgatter, K
Machado, Y
[J]. JOURNAL OF CHEMICAL INFORMATION AND MODELING, 2005, 45 (04) : 1082 - 1100
[9] Stereocontrolled total synthesis of (-)-gleenol using Claisen rearrangement of sterically congested dihydropyran
Nakazaki, Atsuo
Era, Tomohiro
Kobayashi, Susumu
[J]. CHEMISTRY LETTERS, 2008, 37 (07) : 770 - 771
[10] Total Synthesis of (±)-gleenol and (±)-axenol via a functionalized spiro[4.5]decane
Nakazaki, Atsuo
Era, Tomohiro
Kobayashi, Susumu
[J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2007, 55 (11) : 1606 - 1609

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