A general, enantiospecific synthesis of cyclopentanoid monoterpenes (iridoids). The total synthesis of (-)-1-O-methylsweroside aglycon

1984 ◽  
Vol 49 (15) ◽  
pp. 2837-2838 ◽  
Author(s):  
Takafumi Ikeda ◽  
C. Richard Hutchinson
Keyword(s):  
Total Synthesis ◽  
Cyclopentanoid Monoterpenes ◽  
Enantiospecific Synthesis

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).

Synthesis of the spirosesquiterpene (−)-acorenone and related cyclopentanoid monoterpenes

1978 ◽  
Vol 56 (12) ◽  
pp. 1628-1633 ◽  
Author(s):  
Gordon L. Lange ◽  
Eli E. Neidert ◽  
Will J. Orrom ◽  
David J. Wallace
Keyword(s):  
Acetic Acid ◽  
Total Synthesis ◽  
Absolute Configuration ◽  
Optically Active ◽  
Starting Material ◽  
Critical Step ◽  
Naturally Occurring ◽  
Toluenesulfonic Acid ◽  
Methylmagnesium Iodide ◽  
Cyclopentanoid Monoterpenes

The first total synthesis of the spirosesquiterpene (−)-acorenone (1) is described. The critical step involves a spiroannelation of the enamine of aldehyde 11 with 1-methoxy-3-buten-2-one (16) in the presence of acetic acid to give ketone 17. Reaction of 17 with methylmagnesium iodide followed by treatment of the resultant alcohol 18 with p-toluenesulfonic acid in refluxing benzene leads directly to 1 in good overall yield. As the starting material for the preparation of the cyclopentanoid aldehyde 11 was (+)-limonene the final product is optically active and thus the absolute configuration of naturally occurring (−)-acorenone (1) is established. The preparation of a number of other optically active cyclopentanoid monoterpenes (4 and 13) is also described.

Total Synthesis of (+)-Aspidospermidine:  A New Strategy for the Enantiospecific Synthesis of Aspidosperma Alkaloids

2002 ◽  
Vol 124 (45) ◽  
pp. 13398-13399 ◽  
Author(s):  
Joseph P. Marino ◽  
Maria B. Rubio ◽  
Ganfeng Cao ◽  
Alfonso de Dios
Keyword(s):  
Total Synthesis ◽  
New Strategy ◽  
Enantiospecific Synthesis

Enantiospecific Synthesis of Optically Active 6-Methoxytryptophan Derivatives and Total Synthesis of Tryprostatin A1

1997 ◽  
Vol 62 (26) ◽  
pp. 9298-9304 ◽  
Author(s):  
Tong Gan ◽  
Ruiyan Liu ◽  
Peng Yu ◽  
Shuo Zhao ◽  
James M. Cook
Keyword(s):  
Total Synthesis ◽  
Optically Active ◽  
Enantiospecific Synthesis
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