97466-68-7

Basic information

• Product Name: (+/-)-pyrenolide B
• CAS NO: 97466-68-7
• Molecular Weight: 180.203
• Mol File: 97466-68-7.mol

Chemical Properties

• CAS DataBase Reference: (+/-)-pyrenolide B(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-pyrenolide B(97466-68-7)
• EPA Substance Registry System: (+/-)-pyrenolide B(97466-68-7)

Safety Data

• Hazardous Substances Data: 97466-68-7(Hazardous Substances Data)

Upstream product

• 97424-38-9 6-Phenylsulfanyl-1,4,4a,6,7,8a-hexahydro-1,4-methano-naphthalene-5,8-dione 
• 97424-43-6 C₁₇H₂₂O₃ 
• 97424-42-5 C₁₇H₂₄O₄ 
• 97424-46-9 8-Hydroxy-5-methyl-4-oxa-tricyclo[10.2.1.0^2,11]pentadec-13-ene-3,10-dione 
• 21428-54-6 1,4,4a,6,7,8a-hexahydro-1,4-methano-naphthalene-5,8-dione 
• 73674-37-0 (+/-)-2-Methylcyclononanone 
• 4017-57-6 2-oxocyclononanecarboxylic acid ethyl ester 
• 65371-27-9 2-decen-9-olide (Z isomer) 
• 65371-24-6 phoracantholide I 
• 97424-47-0 (E)-5-Methyl-4-oxa-tricyclo[10.2.1.0^2,11]pentadeca-8,13-diene-3,10-dione 
• 97424-41-4 C₂₃H₂₆O₄S 
• 97424-44-7 C₁₇H₂₂O₅ 
• 97424-45-8 C₁₇H₂₄O₅ 
• 97424-40-3 C₁₉H₂₀O₃S 

Relevant articles and documents

Synthesis of (±)-pyrenolide B

In the synthesis of the title compound 12, the important intermediate 7 was obtained in good yield from the easily available ethyl 5,5-ethylenedioxy-2-oxocyclohexane-1-carboxylate (1) via ring enlargement of the bicyclic enol ether 5. Its reduction (NaBH4, CeCl3 in EtOH) and subsequent protection with (t-Bu)Me2Si resulted in the highly functionalized ten-membered lactone 9. Introduction of the (Z)-configurated double bond, followed by deprotection and elimination of H2O, gave (±)-pyrenolide B (12) in 16% overall yield.

Synthesis and Biological Activity of (+/-)-Pyrenolide B

The synthesis and biological activity of (+/-)-pyrenolide B (1) and related compounds are described.The known (Z)-2-decen-9-olide (7) prepared via decan-9-olide (6) from 2-ethoxycarbonylcyclononanone (4) was converted to 9 by the deconjugative process, which, upon oxidation with m-chloroperbenzoic acid, led to the epoxy lactone 10.Base-promoted epoxide ring of 10 and subsequent oxidation furnished keto lactone 8, which, on treatment with phenylselenenyl chloride and subsequent oxidative elimination, provided (+/-)-pyrenolide B (1).The antimicrobial activity od (+/-)-1, 6, 7, 8, 9, 10a, 10b and 11a was examined against fungi and yeast.

TOTAL SYNTHESIS OF (+/-)-PYRENOLIDE B

Synthesis of the title compound is described.