Total Synthesis of the Marine Toxin Polycavernoside A via Selective Macrolactonization of a Trihydroxy Carboxylic Acid

2001 ◽  
Vol 123 (35) ◽  
pp. 8593-8595 ◽  
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

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

Total syntheses and antiproliferative activities of prenostodione and its analogues

2021 ◽  
Author(s):  
Aldahir Ramos Orea ◽  
María Teresa Ramírez-Apan ◽  
Rosa M. Chávez-Santos ◽  
Rodrigo Aguayo-Ortiz ◽  
Clara I Espitia ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Total Synthesis ◽  
Indole Alkaloid ◽  
Total Syntheses ◽  
Antiproliferative Activities

A high-yielding total synthesis of the indole alkaloid prenostodione was completed in 4 steps and 44% overall yield from 1H-indole-3-carboxylic acid. The expedient syntheses of prenostodiones containing distinct substituents at...

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

Synthesis of Optically Active Hydroxyalkyl Cycloheptatrienes: A Key Step in the Total Synthesis of 6,11-Methylene-LXB4

Synlett ◽  
2020 ◽  
Vol 32 (01) ◽  
pp. 45-50
Author(s):  
Udo Nubbemeyer ◽  
Analuisa Nava ◽  
Lukas Trippe ◽  
Andrea Frank ◽  
Lars Andernach ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Total Synthesis ◽  
Structure Elucidation ◽  
Butyl Ester ◽  
Optically Active ◽  
Chiral Hplc ◽  
Reaction Conditions ◽  
Acid Product ◽  
Tert Butyl ◽  
Nabh4 Reduction

AbstractStarting from methyl cycloheptatrienyl-1-carboxylate, 6-acylation was successfully achieved employing glutaryl chloride in the presence of AlCl3 under controlled reaction conditions to furnish keto carboxylic acid product. After protection of this keto carboxylic acid as tert-butyl ester, reagent-controlled enantioselective reductions delivered configuration-defined methyl-6-hydroxylalkyl cycloheptatriene-1-carboxylates with up to 80% ee. Whereas simple NaBH4 reduction of the keto carboxylic acid and subsequent lactonization afforded a methyl-6-tetrahydropyranonyl cycloheptatriene-1-carboxylate. Resolution using chiral HPLC delivered the product enantiomers with up to >99% ee Finally, ECD analyses enabled structure elucidation. The products are used as key intermediates in enantioselective 6,11-methylene-lipoxin B4 syntheses.

Synthesis of the Tetrahydrofuran Ring Part of a Marine Toxin Polycavernoside-A

1994 ◽  
Vol 23 (11) ◽  
pp. 2143-2146 ◽  
Author(s):  
Nobuyuki Hayashi ◽  
Takaaki Mine ◽  
Kenshu Fujiwara ◽  
Akio Murai
Keyword(s):  
Marine Toxin ◽  
Polycavernoside A

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

Total synthesis of (+)-polyoximic acid - cis-3-ethylidene-L-azetidine-2-carboxylic acid

1993 ◽  
Vol 34 (26) ◽  
pp. 4157-4160 ◽  
Author(s):  
Stephen Hanessian ◽  
Jian-Min Fu ◽  
José-Luis Chiara ◽  
Romano Di Fabio
Keyword(s):  
Carboxylic Acid ◽  
Total Synthesis

Total synthesis of (±)-clavam-2-carboxylic acid

1988 ◽  
Vol 29 (13) ◽  
pp. 1609-1612 ◽  
Author(s):  
E. Arribas ◽  
C. Carreiro ◽  
A.M. Valdeolmillos
Keyword(s):  
Carboxylic Acid ◽  
Total Synthesis
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