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.

ChemInform Abstract: Total Synthesis and Determination of the Absolute Configuration of FD-838, a Naturally Occurring Azaspirobicyclic Product.

ChemInform ◽  
2009 ◽  
Vol 40 (47) ◽  
Author(s):  
Yujiro Hayashi ◽  
Kuppusamy Sankar ◽  
Hayato Ishikawa ◽  
Yuriko Nozawa ◽  
Kazutoshi Mizoue ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
Naturally Occurring ◽  
The Absolute

Enzymes in organic synthesis. 36. Synthesis of optically active civet constituent from an enzyme-generated chiral synthon

1987 ◽  
Vol 65 (4) ◽  
pp. 704-707 ◽  
Author(s):  
J. Bryan Jones ◽  
R. Scott Hinks
Keyword(s):  
Acetic Acid ◽  
Organic Synthesis ◽  
Pancreatic Lipase ◽  
Optically Active ◽  
Starting Material ◽  
Porcine Pancreatic Lipase ◽  
Hydrolysis Of ◽  
Enzymes In Organic Synthesis ◽  
Chiral Synthon

A synthesis of the civet constituent, (+)-(S,S)-(cis-6-methyltetrahydropyran-2-yl)acetic acid, is described, in which the key stereochemistry of the chiral starting material is set by an enantiotopically selective, porcine pancreatic lipase-catalyzed, hydrolysis of a meso diester.

Isolation, structure, and synthesis of chenopodanol and the absolute configuration of chenopodene and chenopodanol

1997 ◽  
Vol 75 (6) ◽  
pp. 634-640 ◽  
Author(s):  
Motoo Tori ◽  
Tomonobu Hamaguchi ◽  
Mamiko Aoki ◽  
Masakazu Sono ◽  
Yoshinori Asakawa
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
Active Form ◽  
Optically Active ◽  
Spectroscopic Techniques ◽  
The Absolute

(−)-Chenopodanol (2) has been isolated from the liverwort Marchantiachenopoda and its structure determined by spectroscopic techniques as well as by total synthesis. Chenopodene (1) has also been synthesized in an optically active form, resulting in revision of the originally assigned absolute configuration. Keywords: chenopodanol, chenopodene, liverwort, Marchantiachenopoda, sesquiterpene.

scholarly journals Concise total synthesis of two marine natural nucleosides: trachycladines A and B

2014 ◽  
Vol 10 ◽  
pp. 1681-1685 ◽  
Author(s):  
Haixin Ding ◽  
Wei Li ◽  
Zhizhong Ruan ◽  
Ruchun Yang ◽  
Zhijie Mao ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Starting Material ◽  
Chemoenzymatic Synthesis ◽  
Critical Step ◽  
Adenylate Deaminase

We report the first total synthesis of trachycladines A (10 steps, 34.2% overall yield) and B (11 steps, 35.0% overall yield) by using 5-deoxy-1,2,3-tri-O-acetyl-β-D-ribofuranose as the starting material. The critical step was the SnCl4assisted regio- and steroselective deprotection of perbenzylated 1-O-methyl-5-deoxyribofuranose. The enzyme adenylate deaminase (EC 3.5.4.6) was successfully applied to the chemoenzymatic synthesis of trachycladines B.

Concise Total Synthesis of (+)-Atlanticone C

Synlett ◽  
2020 ◽  
Vol 31 (16) ◽  
pp. 1598-1602 ◽  
Author(s):  
Thorsten Bach ◽  
Johanna Proessdorf ◽  
Andreas Zech ◽  
Christian Jandl
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
Photochemical Reaction ◽  
Enantioselective Total Synthesis ◽  
Naturally Occurring ◽  
The Absolute

The first enantioselective total synthesis of (+)-atlanticone C is described. The complex tricyclic protoilludane core was rapidly assembled by a photochemical reaction cascade starting from an easily accessible indanone precursor (3 steps). Optimization of an enantioselective Corey–Bakshi–Shibata reduction permitted a catalytic chiral reso­lution of the racemic photoproduct (45% over two steps; up to 98% ee). The enantiomerically enriched photoproduct was efficiently transformed into the (+)-enantiomer of atlanticone C (10 steps; 18% yield), and the absolute configuration of naturally occurring (–)-atlanticone C was thereby determined.

ChemInform Abstract: First Total Synthesis and Absolute Configuration of Naturally Occurring (-)-Hyacinthacine A7(Ia) and Its (-)-1-epi-Isomer (Ib).

ChemInform ◽  
2008 ◽  
Vol 39 (39) ◽  
Author(s):  
Isidoro Izquierdo ◽  
Maria T. Plaza ◽  
Juan A. Tamayo ◽  
Victor Yanez ◽  
Daniele Lo Re ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
Naturally Occurring

First total synthesis and absolute configuration of naturally occurring (−)-hyacinthacine A7 and its (−)-1-epi-isomer

Tetrahedron ◽  
2008 ◽  
Vol 64 (20) ◽  
pp. 4613-4618 ◽  
Author(s):  
Isidoro Izquierdo ◽  
María T. Plaza ◽  
Juan A. Tamayo ◽  
Víctor Yáñez ◽  
Daniele Lo Re ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
Naturally Occurring
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