119181-34-9

Upstream product

• 72062-09-0 laurenan-2β-ol 
• 80113-94-6 laurenan-2α-yl acetate 
• 80113-94-6 laurenan-2β-yl acetate 
• 113706-51-7 (2aR,4aS,10aS)-3,3,4a,10a-Tetramethyl-6-oxo-tetradecahydro-pentaleno[1,6-cd]azulene-7-carbonitrile 
• 113706-47-1 4-((1S,3aR,5aR)-1,4,4,5a-Tetramethyl-1,2,3,3a,4,5,5a,6-octahydro-cyclopenta[c]pentalen-1-yl)-butyric acid methyl ester 
• 113706-35-7 4-((1S,3aR,5aR,8R)-8-Methoxy-1,4,4,5a-tetramethyl-decahydro-cyclopenta[c]pentalen-1-yl)-butyric acid methyl ester 
• 113706-45-9 4-((1S,3aR,5aR,8R)-8-Acetoxy-1,4,4,5a-tetramethyl-decahydro-cyclopenta[c]pentalen-1-yl)-butyric acid methyl ester 
• 72062-09-0 laurenan-2α-ol 
• 113706-50-6 4-((1S,3aR,5aR,8R)-8-Hydroxy-1,4,4,5a-tetramethyl-decahydro-cyclopenta[c]pentalen-1-yl)-butyric acid methyl ester 
• 89949-65-5 (3aR,5aR,8R)-8-Methoxy-4,4,5a-trimethyl-octahydro-cyclopenta[c]pentalen-1-one 
• 82995-43-5 (3aR,5aR)-8-Hydroxy-4,4,5a-trimethyl-octahydro-cyclopenta[c]pentalen-1-one 
• 113706-44-8 (E)-4-((1R,3aR,5aR,8R)-8-Methoxy-1,4,4,5a-tetramethyl-decahydro-cyclopenta[c]pentalen-1-yl)-but-2-enoic acid methyl ester 
• 110418-84-3 4-((1S,3aR,5aS)-1,4,4,5a-Tetramethyl-7-oxo-decahydro-cyclopenta[c]pentalen-1-yl)-butyraldehyde 
• 113706-46-0 4-((1S,3aR,5aR,8R)-8-Hydroxy-1,4,4,5a-tetramethyl-decahydro-cyclopenta[c]pentalen-1-yl)-butyric acid 

Relevant academic research and scientific papers

The Chemistry of Laurenene. XVI. Investigation of the Mechanism of a Cationic Rearrangement

Some aspects of the mechanism of the acid-induced rearrangement of laurenan-2β-ol have been deduced from deuterium-labelling studies.A key intermediate arises from two pathways, one involving a 1,4- and one a 1,5-hydride shift.Formation of this intermediate is partially suppressed by substitution of the migrating hydrogen by a deuterium.A proposed pathway which involves a 1,3-methyl migration has been disproved, and scrambling and loss of deuterium label has been accounted for in terms of equilibria involving lauren-1-ene and another previously reported rearrangement product.The rearrangement is strongly promoted in dichloromethane, and the product composition is highly solvent-dependent.

The Chemistry of Laurenene. X A New Carbon Skeleton by Rearrangement of Laurenan-2β-ol

Treatment of laurenan-2β-ol (2) with trifluoroacetic acid in dichloromethane at 0 deg gives as the major product the rearranged alkene (4).This compound has a new carbon-ring system containing three five-membered rings and one six-membered ring.The structure of (4) has been determined by a range of n.m.r. techniques applied to (4) and selected derivatives.Deuterium-labelling experiments have established that the rearrangement proceeds to a remote part of the molecule and then returns to its starting point.

TOTAL SYNTHESIS OF (+/-)-LAUREN-1-ENE, THE UNIQUE FENESTRANE DITERPENE

The first total synthesis of (+/-)-lauren-1-ene (1a), the unique diterpene containing the (5.5.5.7)fenestrane ring system, has been achieved starting from the aldol 4, the intermediate in a synthesis of (+/-)-silphinene.

The Chemistry of Lauren-1-ene. III Synthesis and Properties of Laurenane and 1βH-Laurenane

The saturated hydrocarbons laurenane (3) and 1βH-laurenane (4) have been synthesized.Assignments of their 13C n.m.r. and 1H n.m.r. spectra are reported and used, with the aid of lanthanide shift reagents, to investigate conformational mobility of these substituted fenestranes.Some examples of long-range 13C n.m.r. substituent effects of the ε and ζ types have been noted.