78148-92-2Relevant academic research and scientific papers
Intramolecular Photocycloadditions-Cyclobutane Fragmentation: Total Synthesis of (+/-)-Pentalenene, (+/-)-Pentalenic Acid, and (+/-)-Deoxypentalenic Acid
Crimmins, Michael T.,DeLoach, Joe A.
, p. 800 - 806 (1986)
Pentalenene, pentalenic acid, and deoxypentalenic acid, important metabolites in the biosynthesis of the pentalenolactones, have been synthesized from methyl isobutyrate through a common intermediate.The initial key stp involves a novel conjugate addition
Intramolecular Photocycloaddition-Cyclobutane Fragmentation: A Highly Stereoselective Total Synthesis of (+/-)-Pentalenic Acid
Crimmins, Michael T.,DeLoach, Joe A.
, p. 2076 - 2077 (2007/10/02)
An efficient total synthesis of pentalenic acid has been accomplished by utilizing an intramolecular photocycloaddition-cyclobutane fragmentation as the key reaction sequence.
SYNTHESIS OF PENTALENIC ACID THROUGH BIOGENETIC LIKE CYCLIZATION OF HUMULENE
Sakai, Kazuya,Ohtsuka, Toshikazu,Misumi, Shunjiro,Shirahama, Haruhisa,Matsumoto, Takeshi
, p. 355 - 358 (2007/10/02)
Humulene furnished 4,7-epoxy-3-methylene-7,10,10-trimethyl-11-bicycloundecanol 9 in 34percent yield employing oxymercuration as a key step.On treatment with BF3.OEt2, 7,11-dihydroxy-3,7,10,10-tetramethyl-3-bicycloundecene, which was derived from 9 by ether cleavage, afforded 10α-hydroxy-pentalenene 13 (20percent) along with four byproducts.Oxidation of allylic methyl group of 13 gave methyl pentalenate in 13percent yield from 9.
