Non-natural Elemane as the "Stepping Stone" for the Synthesis of Germacrane and Guaiane Sesquiterpenes

被引：23

作者：

Anagnostaki, Elissavet E. ^{[1
]}

Zografos, Alexandros L. ^{[1
]}

机构：

[1] Aristotle Univ Thessaloniki, Dept Chem, Organ Chem Lab, Thessaloniki 54124, Greece

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 01期

关键词：

CATALYZED ALLYLIC OXIDATION; LACTONES; RING; REARRANGEMENT; THAPSIGARGINS; CONSTRUCTION; CONFORMATION; ORIGIN;

D O I：

10.1021/ol3031999

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of hydroxyelemane 5 from (R)-carvone and its utilization as a common synthetic scaffold to produce structurally diverse germacrane and guaiane sesquiterpenes are described. A highly enantio- and stereoselective biomimetic tandem oxy-Cope/ene rearrangement was used as the key reaction to access the 10-membered macrocyclic core of germacranes and the condensed 5-7 carbocycles of guaiane sesquiterpenes. Additionally, reactions of furanoguaianes under acidic or oxidizing reagents have been investigated, and preliminary results of these conversions are presented.

引用

页码：152 / 155

页数：4

共 49 条

[1] Recent Mechanistic Insights in the Singlet Oxygen Ene Reaction [J].

Alberti, Mariza N. ;

Orfanopoulos, Michael .

SYNLETT, 2010, (07) :999-1026

[2] Total synthesis of five thapsigargins:: Guaianolide natural products exhibiting sub-nanomolar SERCA inhibition [J].

Andrews, Stephen P. ;

Ball, Matthew ;

Wierschem, Frank ;

Cleator, Ed ;

Oliver, Steven ;

Hoegenauer, Klemens ;

Simic, Oliver ;

Antonello, Alessandra ;

Huenger, Udo ;

Smith, Martin D. ;

Ley, Steven V. .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (20) :5688-5712

[3] Diastereoselective construction of quaternary carbons directed via macrocyclic ring conformation:: Formal synthesis of (-)-mesembrine [J].

Arns, Steve ;

Lebrun, Marie-Eve ;

Grise, Christiane M. ;

Denissova, Irina ;

Barriault, Louis .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (24) :9314-9322

[4] Cascading pericyclic reactions: building complex carbon frameworks for natural product synthesis [J].

Arns, Steve ;

Barriault, Louis .

CHEMICAL COMMUNICATIONS, 2007, (22) :2211-2221

[5] Total synthesis of (+)-arteanniun M using the tandem oxy-cope/ene reaction [J].

Barriault, L ;

Deon, DH .

ORGANIC LETTERS, 2001, 3 (12) :1925-1927

[6] Benzylic and Allylic Oxidations with Bis(trifluoroacetoxyiodo)benzene and tert-Butyl Hydroperoxide [J].

Catir, Mustafa ;

Kilic, Hamdullah .

SYNLETT, 2010, (09) :1319-1322

[7] A Trojan Horse in Drug Development: Targeting of Thapsigargins Towards Prostate Cancer Cells [J].

Christensen, S. Brogger ;

Skytte, Dorthe Mondrup ;

Denmeade, Samuel R. ;

Dionne, Craig ;

Moller, Jesper Vuust ;

Nissen, Poul ;

Isaacs, John T. .

ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY, 2009, 9 (03) :276-294

[8] ALLYLIC OXIDATION OF OLEFINS WITH CHROMIUM TRIOXIDE-PYRIDINE COMPLEX [J].

DAUBEN, WG ;

LORBER, M ;

FULLERTON, DS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (11) :3587-+

[9] Molecular pharmacology and pharmacogenomics of artemisinin and its derivatives in cancer cells [J].

Efferth, T .

CURRENT DRUG TARGETS, 2006, 7 (04) :407-421

[10] A brief and stereoselective synthesis of limonoid models, with antifeedant activity against Locusts migratoria [J].

Fernandez-Mateos, A. ;

Ramos Silvo, A. I. ;

Gonzalez, R. Rubio ;

Simmonds, A. S. J. .

TETRAHEDRON, 2006, 62 (33) :7809-7816

← 1 2 3 4 5 →