Total Synthesis of (−)-Polycavernoside A: Suzuki–Miyaura Coupling Approach

2012 ◽  
Vol 14 (12) ◽  
pp. 3186-3189 ◽  
Author(s):  
Yusuke Kasai ◽  
Takanori Ito ◽  
Makoto Sasaki
Keyword(s):  
Total Synthesis ◽  
Polycavernoside A ◽  
Coupling Approach

Convergent Total Synthesis of Principinol D, a Rearranged Kaurane Diterpenoid

2019 ◽  
Author(s):  
Timothy Newhouse ◽  
Aneta Turlik ◽  
Yifeng Chen ◽  
Anthony Scruse
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Late Stage ◽  
Membered Ring ◽  
Entry Point ◽  
Ketone Reduction ◽  
Coupling Approach

<div> <p>The total synthesis of principinol D, a rearranged kaurane diterpenoid, is reported. This grayanane natural product is constructed via a convergent fragment coupling approach, wherein the central 7-membered ring is synthesized at a late stage. The bicyclo[3.2.1]octane fragment is accessed by a Ni-catalyzed α-vinylation reaction. Strategic reductions include a diastereoselective SmI<sub>2</sub>-mediated ketone reduction with PhSH and a new protocol for selective ester reduction in the presence of ketones. The convergent strategy reported herein may be an entry point to the larger class of kaurane diterpenoids.</p> </div>

ChemInform Abstract: Total Synthesis of the Marine Toxin Polycavernoside A (I) via Selective Macrolactonization of a Trihydroxy Carboxylic Acid.

ChemInform ◽  
2010 ◽  
Vol 32 (52) ◽  
pp. no-no
Author(s):  
James D. White ◽  
Paul R. Blakemore ◽  
Cindy C. Browder ◽  
Jian Hong ◽  
Christopher M. Lincoln ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Total Synthesis ◽  
Marine Toxin ◽  
Polycavernoside A

scholarly journals Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for the Enantioselective Total Synthesis of Mavacuran Alkaloids

2019 ◽  
Author(s):  
Maxime Jarret ◽  
Victor Turpin ◽  
Aurélien Tap ◽  
Jean-Francois Gallard ◽  
Cyrille Kouklovsky ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Indole Alkaloids ◽  
Oxidative Cyclization ◽  
Total Syntheses ◽  
Enantioselective Total Synthesis ◽  
Biosynthetic Precursor ◽  
Monoterpene Indole Alkaloids ◽  
Coupling Approach

We report the enantioselective total syntheses of mavacurans alkaloids, (+)-taberdivarine H, (+)-16-hydoxymethyl-pleiocarpamine, (+)-16-epi-pleiocarpamine, and their postulated biosynthetic precursor 16-formyl-pleiocarpamine. This family of monoterpene indole alkaloids is a target of choice since some of its members are subunits of intricate bisindole alkaloids such as bipleiophylline. Inspired by the biosynthetic hypothesis, we explored an oxidative coupling approach from the geissoschizine framework to form the N1-C16 bond. Quaternization of the aliphatic nitrogen was key to achieve the oxidative coupling induced by KHMDS/I<sub>2 </sub>since<sub> </sub>it hides the nucleophilicity of the aliphatic nitrogen and locks the required cis conformation.

Total Synthesis of Polycavernoside A, A Lethal Toxin of the Red AlgaPolycavernosatsudai

2005 ◽  
Vol 70 (14) ◽  
pp. 5449-5460 ◽  
Author(s):  
Paul R. Blakemore ◽  
Cindy C. Browder ◽  
Jian Hong ◽  
Christopher M. Lincoln ◽  
Pavel A. Nagornyy ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Lethal Toxin ◽  
Polycavernoside A

scholarly journals Convergent Total Synthesis of Principinol D, a Rearranged Kaurane Diterpenoid

2019 ◽  
Author(s):  
Timothy Newhouse ◽  
Aneta Turlik ◽  
Yifeng Chen ◽  
Anthony Scruse
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Late Stage ◽  
Membered Ring ◽  
Entry Point ◽  
Ketone Reduction ◽  
Coupling Approach

<div> <p>The total synthesis of principinol D, a rearranged kaurane diterpenoid, is reported. This grayanane natural product is constructed via a convergent fragment coupling approach, wherein the central 7-membered ring is synthesized at a late stage. The bicyclo[3.2.1]octane fragment is accessed by a Ni-catalyzed α-vinylation reaction. Strategic reductions include a diastereoselective SmI<sub>2</sub>-mediated ketone reduction with PhSH and a new protocol for selective ester reduction in the presence of ketones. The convergent strategy reported herein may be an entry point to the larger class of kaurane diterpenoids.</p> </div>

Convergent Total Synthesis of (–)-Principinol D, a Rearranged Kaurane Diterpenoid

2019 ◽  
Author(s):  
Aneta Turlik ◽  
Yifeng Chen ◽  
Anthony Scruse ◽  
Timothy Newhouse
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Late Stage ◽  
Membered Ring ◽  
Entry Point ◽  
Ketone Reduction ◽  
Wide Range ◽  
Coupling Approach

<div> <p>The total synthesis of principinol D, a rearranged kaurane diterpenoid, is reported. This grayanane natural product was constructed via a convergent fragment coupling approach, wherein the central 7-membered ring was synthesized at a late stage. The <a>bicyclo</a>[3.2.1]octane fragment is accessed by a Ni-catalyzed α-vinylation reaction, followed by a diastereoselective SmI<sub>2</sub>-mediated ketone reduction. The convergent strategy reported herein may be an entry point to a wide range of kaurane diterpenoids. </p> </div>

Total Synthesis of Polycavernoside A (I), a Lethal Toxin of the Red Alga Polycavernosa tsudai.

ChemInform ◽  
2005 ◽  
Vol 36 (49) ◽  
Author(s):  
Paul R. Blakemore ◽  
Cindy C. Browder ◽  
Jian Hong ◽  
Christopher M. Lincoln ◽  
Pavel A. Nagornyy ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Red Alga ◽  
Lethal Toxin ◽  
Polycavernoside A

scholarly journals Total Synthesis of Polycavernoside A.

1999 ◽  
Vol 57 (11) ◽  
pp. 993-1003 ◽  
Author(s):  
Kenshu Fujiwara ◽  
Akio Murai
Keyword(s):  
Total Synthesis ◽  
Polycavernoside A
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