ChemInform Abstract: Concise Asymmetric Formal Synthesis of Pyrrolopiperazinone Natural Products by Tandem Cross Metathesis/Intramolecular Aza-Conjugate Addition.

ChemInform ◽  
2011 ◽  
Vol 42 (24) ◽  
pp. no-no
Author(s):  
Su-Hyun Kwon ◽  
Hyo-Jun Lee ◽  
Chang-Woo Cho
Keyword(s):  
Natural Products ◽  
Conjugate Addition ◽  
Formal Synthesis ◽  
Cross Metathesis

scholarly journals Metathesis Transformations of Natural Products: Cross-Metathesis of Natural Rubber and Mandarin Oil by Ru-Alkylidene Catalysts

Molecules ◽  
2012 ◽  
Vol 17 (5) ◽  
pp. 6001-6010 ◽  
Author(s):  
Araceli Martínez ◽  
Selena Gutiérrez ◽  
Mikhail A. Tlenkopatchev
Keyword(s):  
Natural Products ◽  
Natural Rubber ◽  
Cross Metathesis

The Rearrangement of 2,3-Epoxysulfonates and Its Application to Natural Products Syntheses: Formal Synthesis of (-)-Aphanorphine and Total Syntheses of (-)-α-Herbertenol and (-)-Herbertenediol.

ChemInform ◽  
2003 ◽  
Vol 34 (47) ◽  
Author(s):  
Yasuyuki Kita ◽  
Junko Futamura ◽  
Yusuke Ohba ◽  
Yoshinari Sawama ◽  
Jnaneshwara K. Ganesh ◽  
...  
Keyword(s):  
Natural Products ◽  
Formal Synthesis ◽  
Total Syntheses

Formal Synthesis of (±)-Aplykurodinone-1 Based on the Indium-Catalyzed Conia-Ene Reaction

Synlett ◽  
2020 ◽  
Vol 31 (14) ◽  
pp. 1404-1408
Author(s):  
Xiaoji Wang ◽  
Liping Wang ◽  
Shuangping Huang ◽  
Yi Zhou ◽  
Hesheng Xiao ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Selenium Dioxide ◽  
Ring Closing Metathesis ◽  
Formal Synthesis ◽  
Ene Reaction ◽  
Synthetic Strategy

A concise formal synthesis of (±)-aplykurodinone-1 starting from a commercially available material and based on the indium-catalyzed Conia-ene reaction has been accomplished. The synthesis features a Riley selenium dioxide oxidation, a Krapcho dealkoxycarbonylation, and a ring-closing metathesis approach. The synthetic strategy was also supported by a Saegusa oxidation and a classic Michael 1,4-conjugate addition.

scholarly journals Expedient Access to Enantiopure Cyclopentanic Natural Products: Total Synthesis of (-)-Cyclonerodiol

2015 ◽  
Vol 10 (1) ◽  
pp. 1934578X1501000
Author(s):  
Carmen Pérez Morales ◽  
M. Mar Herrador ◽  
José F. Quílez del Moral ◽  
Alejandro F. Barrero
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Radical Cyclization ◽  
Formal Synthesis ◽  
Common Precursor ◽  
Enantiospecific Synthesis ◽  
Optically Pure

Following the principles of collective total synthesis, a number of natural products sharing an optically pure, multifunctional, cyclopentanic core were synthesized from a common precursor: plinol A (1). This intermediate was efficiently obtained in only four steps from (-)-linalool (2) using as the key step a Ti(III)-mediated diastereoselective radical cyclization. The feasibility of this approach was confirmed with the expedient enantiospecific synthesis of cyclonerodiol (3), and the formal synthesis of chocol G (4) and piperitone (5).

scholarly journals Copper-catalyzed enantioselective conjugate addition of organometallic reagents to challenging Michael acceptors

2020 ◽  
Vol 16 ◽  
pp. 212-232 ◽  
Author(s):  
Delphine Pichon ◽  
Jennifer Morvan ◽  
Christophe Crévisy ◽  
Marc Mauduit
Keyword(s):  
Natural Products ◽  
Conjugate Addition ◽  
Catalytic Transformation ◽  
Chiral Molecules ◽  
Catalytic Systems ◽  
Organometallic Reagents ◽  
Recent Advances ◽  
Wide Range ◽  
Michael Acceptors

The copper-catalyzed enantioselective conjugate addition (ECA) of organometallic nucleophiles to electron-deficient alkenes (Michael acceptors) represents an efficient and attractive methodology for providing a wide range of relevant chiral molecules. In order to increase the attractiveness of this useful catalytic transformation, some Michael acceptors bearing challenging electron-deficient functions (i.e., aldehydes, thioesters, acylimidazoles, N-acyloxazolidinones, N-acylpyrrolidinones, amides, N-acylpyrroles) were recently investigated. Remarkably, only a few chiral copper-based catalytic systems have successfully achieved the conjugate addition of different organometallic reagents to these challenging Michael acceptors, with excellent regio- and enantioselectivity. Furthermore, thanks to their easy derivatization, the resulting chiral conjugated products could be converted into various natural products. The aim of this tutorial review is to summarize recent advances accomplished in this stimulating field.

The Spongistatins: Architecturally Complex Natural Products—Part One: A Formal Synthesis of (+)-Spongistatin 1 by Construction of an Advanced ABCD Fragment

2001 ◽  
Vol 113 (1) ◽  
pp. 197-201 ◽  
Author(s):  
Amos B. Smith III ◽  
Victoria A. Doughty ◽  
Qiyan Lin ◽  
Linghang Zhuang ◽  
Mark D. McBriar ◽  
...  
Keyword(s):  
Natural Products ◽  
Formal Synthesis ◽  
Spongistatin 1

Synthetic approaches to [5,6]-benzannulated spiroketal natural products

2011 ◽  
Vol 84 (6) ◽  
pp. 1379-1390 ◽  
Author(s):  
Michael C. McLeod ◽  
Margaret A. Brimble ◽  
Dominea C. K. Rathwell ◽  
Zoe E. Wilson ◽  
Tsz-Ying Yuen
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Electronic Properties ◽  
Late Stage ◽  
Biologically Active ◽  
Formal Synthesis ◽  
Berkelic Acid ◽  
Synthetic Approaches

Studies toward the synthesis of three biologically active [5,6]-benzannulated spiroketal natural products are described. The first total synthesis of paecilospirone is reported, employing a late-stage, pH-neutral spiroketalization. A formal synthesis of γ-rubromycin is described, where the spiroketal moiety is formed by delicate manipulation of the electronic properties of the spirocyclization precursor. Finally, model work toward the total synthesis of berkelic acid is summarized, introducing a novel Horner–Wadsworth–Emmons/oxa-Michael (HWE/oxa-M) cascade to access the spiroketal precursor.

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