Concise syntheses of eburnane indole alkaloids

被引：37

作者：

Zhou, Qilong ^{[1
,2
]}

Dai, Xiang ^{[1
,2
]}

Song, Hao ^{[3
,4
,5
]}

He, Huan ^{[3
,4
,5
]}

Wang, Xiaobei ^{[3
,4
,5
]}

Liu, Xiao-Yu ^{[3
,4
,5
]}

Qin, Yong ^{[3
,4
,5
]}

机构：

[1] Chongqing Univ, Sch Pharmaceut Sci, Chongqing 401331, Peoples R China

[2] Chongqing Univ, Innovat Drug Res Ctr, Chongqing 401331, Peoples R China

[3] Sichuan Univ, West China Sch Pharm, Minist Educ, Key Lab Drug Targeting & Drug Delivery Syst, Chengdu 610041, Sichuan, Peoples R China

[4] Sichuan Univ, West China Sch Pharm, Sichuan Engn Lab Plant Sourced Drug, Chengdu 610041, Sichuan, Peoples R China

[5] Sichuan Univ, West China Sch Pharm, Res Ctr Drug Ind Technol, Chengdu 610041, Sichuan, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 68期

基金：

中国国家自然科学基金;

关键词：

KOPSIA-LARUTENSIS; ABSOLUTE-CONFIGURATION; NATURAL-PRODUCTS; FORMAL SYNTHESIS; EBURNAMINOL; DERIVATIVES; PAUCIFLORA; GRIFFITHII; LEAVES;

D O I：

10.1039/c8cc05374j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The asymmetric divergent syntheses of a group of C20 ethyl oxo-functionalized eburnane alkaloids, (-)-eburnaminol (5), (+)-larutenine (6), (-)-terengganensine B (7), (-)-strempeliopine (8), and (-)-terengganensine A (9), have been achieved. The key step in the assembly of the complex ring system of the target molecules is a photoredox catalytic nitrogen-centered radical cascade reaction, which allows the regioselective and stereoselective construction of the B, C, and D rings and the installation of the C21 chirality of the eburnane alkaloid skeleton in one pot.

引用

页码：9510 / 9512

页数：3

共 33 条

[1] Photoredox-Initiated Radical Cascades Enabling Collective Synthesis of 33 Natural Products
Alabugin, Igor V.
Harris, Trevor
[J]. CHEM, 2017, 2 (06): : 753 - 755
[2] EBURNAMINOL AND LARUTENSINE, ALKALOIDS FROM KOPSIA-LARUTENSIS
AWANG, K
PAIS, M
SEVENET, T
SCHALLER, H
NASIR, AM
HAMID, A
HADI, A
[J]. PHYTOCHEMISTRY, 1991, 30 (09) : 3164 - 3167
[3] Application of Cross-Conjugated Heteroaromatic Betaines to the Synthesis of the Schizozygane Alkaloid (±)-Strempeliopine
Bobeck, Drew R.
Lee, Hyoung Ik
Flick, Andrew C.
Padwa, Albert
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (19) : 7389 - 7402
[4] Organocatalytic conjugate addition of malonates to α,β-unsaturated aldehydes:: Asymmetric formal synthesis of (-)-paroxetine, chiral lactams, and lactones
Brandau, Sven
Landa, Aitor
Franzen, Johan
Marigo, Mauro
Jorgensen, Karl Anker
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) : 4305 - 4309
[5] SYNTHESIS OF ARISTOTELIA-TYPE ALKALOIDS .12. TOTAL SYNTHESIS OF (-)-TASMANINE - STEREOELECTRONIC FACTORS THAT CONTROL THE REARRANGEMENT OF 3H-INDOL-3-OL DERIVATIVES TO OXINDOLES (= 1,3-DIHYDRO-2H-INDOL-2-ONES) OR TO PSEUDOINDOXYLS (= 1,2-DIHYDRO-3H-INDOL-3-ONES)
GULLER, R
BORSCHBERG, HJ
[J]. HELVETICA CHIMICA ACTA, 1993, 76 (05) : 1847 - 1862
[6] STEREOSPECIFIC TOTAL SYNTHESIS OF (+/-)-STREMPELIOPINE
HAJICEK, J
TROJANEK, J
[J]. TETRAHEDRON LETTERS, 1981, 22 (30) : 2927 - 2928
[7] ON ALKALOIDS .52. (-)-STREMPELIOPINE - STEREOSELECTIVE TOTAL SYNTHESIS AND THE DETERMINATION OF ABSOLUTE-CONFIGURATION
HAJICEK, J
TROJANEK, J
[J]. COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1986, 51 (08) : 1731 - 1742
[8] Kam T. S., 1999, ALKALOIDS, V14, P350
[9] Alkaloids from Kopsia pauciflora
Kam, TS
Arasu, L
Yoganathan, K
[J]. PHYTOCHEMISTRY, 1996, 43 (06) : 1385 - 1387
[10] KAM TS, 1993, PHYTOCHEMISTRY, V33, P921, DOI 10.1016/0031-9422(93)85305-B

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