75100-60-6

Upstream product

• 124-83-4 D-(+)-camphoric acid 
• 68510-42-9 (+)-(1R,3S)-1,2,2-Trimethyl-1,3-bis(hydroxymethyl)cyclopentane 
• 15797-21-4 dimethyl (1R,3S)-1,2,2-trimethylcyclopentane-1,3-dicarboxylate 
• 1519-21-7 2-phenylbutyric anhydride 
• 75110-98-4 Acetic acid (1S,3R)-3-((R)-1-hydroxy-ethyl)-2,2,3-trimethyl-cyclopentylmethyl ester 
• 75100-54-8 (+)-(1R,3S,1'R)-3-acetoxymethyl-1-(1',2'-epoxyethyl)-1,2,2-trimethylcyclopentane 
• 75100-58-2 (S)-1-((1R,3S)-3-Hydroxymethyl-1,2,2-trimethyl-cyclopentyl)-ethanol 
• 75100-59-3 Acetic acid (1S,3R)-3-((S)-1-hydroxy-ethyl)-2,2,3-trimethyl-cyclopentylmethyl ester 
• 73616-62-3 Acetic acid (1S,3R)-3-formyl-2,2,3-trimethyl-cyclopentylmethyl ester 
• 73616-65-6 (+/-)-(1S,3S)-3-acetoxymethyl-1,2,2-trimethyl-1-vinylcyclopentane 
• 73616-61-2 Acetic acid (1S,3R)-3-hydroxymethyl-2,2,3-trimethyl-cyclopentylmethyl ester 
• 75100-54-8 (+)-(1R,3S,1'S)-3-acetoxymethyl-1-(1',2'-epoxyethyl)-1,2,2-trimethylcyclopentane 
• 75110-97-3 (R)-1-((1R,3S)-3-Hydroxymethyl-1,2,2-trimethyl-cyclopentyl)-ethanol 

Relevant academic research and scientific papers

CHEMICAL TRANSFORMATION OF TERPENOIDS. I. SYNTHESES OF (3S)-1-VINYL-, (3S)-1-HYDROXYPROPENYL-, AND (3S)-1-EPOXYETHYL-1,2,2-TRIMETHYLCYCLOPENTANE DERIVATIVES FROM d-CAMPHOR VIA d-CAMPHORIC ACID

As part of a series of studies on the transformation of terpenoids, four 1,2,2-trimethylcyclopentane derivatives, i.e., (+)-(1S,3S)-3-acetoxymethyl-1,2,2-trimethyl-1-vinylcyclopentane (5), (+)-(1S,3S)-3-acetoxymethyl-1-(3'-hydroxypropenyl)-1,2,2-trimethylcyclopentane (7), (+)-(1R,3S,1'S)-3-acetoxymethyl-1-(1',2'-epoxyethyl)-1,2,2-trimethylcyclopentane (8), and (+)-(1R,3S,1'R)-3-acetoxymethyl-1-(1',2'-epoxyethyl)-1,2,2-trimethylcyclopentane (9), were synthesized from d-camphor (1) via d-camphoric acid (2).All four compounds (5,7,8,9) retain the C-4 configuration of d-camphor at their C-3 positions.Keywords: - d-camphor; d-camphoric acid; 1-vinyl-1,2,2-trimethylcyclopentane; 1-hydroxypropenyl-1,2,2-trimethylcyclopentane; 1-epoxyethyl-1,2,2-trimethylcyclopentane; Horeau's method

SUCCESSIVE METHYL MIGRATIONS OCCURING IN THE ACID TREATMENT OF 1-EPOXYETHYL-1,2,2-TRIMETHYL-CYCLOPENTANE DERIVATIVE

Acid treatment of (1R,3S,1'S)-1-(1',2'-epoxyethyl)-1,2,2-trimethyl-3-acetoxymethyl-cyclopentane (6) has been shown to yield three products (8, 9, 10), among which 8 and 9 are 1-oxa-bicyclooctane derivatives formed via successive methyl migrations followed by an oxorane ring closure.