Rapid Construction of the ABC Ring System in the Daphniphyllum Alkaloid Daphniyunnine C

被引：46

作者：

Yao, Yanmin

Liang, Guangxin ^{[1
]}

机构：

[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 21期

基金：

中国国家自然科学基金;

关键词：

STEREOSPECIFIC TOTAL-SYNTHESIS; SARPAGINE INDOLE ALKALOIDS; GENERAL-APPROACH; TETRACYCLIC CORE; DAPHNILACTONE-B; VINYL HALIDES; SKELETON; METATHESIS; WELL;

D O I：

10.1021/ol3026395

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and scalable synthesis of the ABC ring system common to the calyciphylline A-type alkaloids has been developed. The tricyclic core of the alkaloids features a bowl-shaped [6-6-5] skeleton with five stereogenic centers including an all-carbon quaternary center. It was constructed rapidly from a readily available carvone derivative through a seven-step sequence involving an aza-Michael addition and Pd-catalyzed enolate alpha-vinylation as key steps.

引用

收藏

页码：5499 / 5501

页数：3

相关论文

共 43 条

[1] Synthesis of the Tetracyclic Core of Daphnilactone B-Type and Yuzurimine-Type Alkaloids [J].

Belanger, Guillaume ;

Boudreault, Jonathan ;

Levesque, Francois .

ORGANIC LETTERS, 2011, 13 (23) :6204-6207

[2] The first enantiospecific synthesis of (-)-koumidine via the intramolecular palladium-catalyzed enolate driven cross coupling reaction.: The stereospecific introduction of the 19-(Z) ethylidene side chain [J].

Cao, H ;

Yu, JM ;

Wearing, XYZ ;

Zhang, CC ;

Liu, XX ;

Deschamps, J ;

Cook, JM .

TETRAHEDRON LETTERS, 2003, 44 (43) :8013-8017

[3] Synthesis of the Core Ring System of the Yuzurimine-Type Daphniphyllum Alkaloids by Cascade Condensation, Cyclization, Cycloaddition Chemistry [J].

Coldham, Iain ;

Watson, Luke ;

Adams, Harry ;

Martin, Nathaniel G. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (07) :2360-2366

[4] Cascade Cyclization, Dipolar Cycloaddition to Bridged Tricyclic Amines Related to the Daphniphyllum Alkaloids [J].

Coldham, Iain ;

Burrell, Adam J. M. ;

Guerrand, Helene D. S. ;

Oram, Niall .

ORGANIC LETTERS, 2011, 13 (06) :1267-1269

[5]

COREY EJ, 1975, TETRAHEDRON LETT, P2647

[6] Enantioselective total synthesis of briarellins E and F: The first total syntheses of briarellin diterpenes [J].

Corminboeuf, O ;

Overman, LE ;

Pennington, LD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) :6650-6652

[7] A Unified Strategy for Enantioselective Total Synthesis of Cladiellin and Briarellin Diterpenes: Total Synthesis of Briarellins E and F and the Putative Structure of Alcyonin and Revision of Its Structure Assignment [J].

Corminboeuf, Olivier ;

Overman, Larry E. ;

Pennington, Lewis D. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) :5458-5470

[8] Expedient Construction of the [7-5-5] All-Carbon Tricyclic Core of the Daphniphyllum Alkaloids Daphnilongeranin B and Daphniyunnine D [J].

Darses, Benjamin ;

Michaelides, Iacovos N. ;

Sladojevich, Filippo ;

Ward, John W. ;

Rzepa, Paula R. ;

Dixon, Darren J. .

ORGANIC LETTERS, 2012, 14 (07) :1684-1687

[9] Tandem double-intramolecular [4+2]/[3+2] cycloadditions of nitroalkenes. Studies toward a total synthesis of daphnilactone B: Piperidine ring construction [J].

Denmark, SE ;

Baiazitov, RY .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (02) :593-605

[10] Alkaloids from the leaves of Daphniphyllum longeracemosum [J].

Di, Ying-Tong ;

He, Hong-Ping ;

Lu, Yang ;

Yi, Ping ;

Li, n Li ;

Wu, Li ;

Hao, Xiao-Jiang .

JOURNAL OF NATURAL PRODUCTS, 2006, 69 (07) :1074-1076

← 1 2 3 4 5 →