37841-93-3

Upstream product

• 37841-91-1 (+)-isovelleral 
• 336101-95-2 (1aR,3aR,6aS,6bR)-1a-(hydroxymethyl)-5,5,6b-trimethyl-1,1a,3a,4,5,6,6a,6b-octahydrocyclopropa[e]inden-2-yl trifluoromethanesulfonate 
• 336101-91-8 (1aS,3aR,6aS,6bR)-5,5,6b-trimethyl-1a-[(1E)-propenyl]-1,1a,3a,4,5,6,6a,6b-octahydrocyclopropa[e]inden-2(1H)-yl trifluoromethanesulfonate 
• 336101-85-0 (1S,4aS,7R,8aS)-7-allyl-3,3,8a-trimethyl-6-octadecahydro-1-naphthalenyl methanesulfonate 
• 336101-88-3 (1aS,3aS,6aS,6bR)-5,5,6b-trimethyl-1a-[(1E)-propenyl]-octahydrocyclopropa[e]inden-2(1H)-one 
• 336102-08-0 (3R,4aS,5S)-3-allyl-5-{[tert-butyl(dimethyl)silyl]oxy}-4a,7,7-trimethyl-4,4,a,5,6,7,8-hexahydro-2(3H)-naphthalenone 
• 336102-07-9 (4aS,5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-4a,7,7-trimethyl-4,4,a,5,6,7,8-hexahydro-2(3H)-naphthalenone 
• 336101-96-3 (1aS,3aS,8aS,8bR)-7,7,8b-trimethyl-5a,6,7,8,8a,8b-hexadrocyclopropa[e]indeno[5,6-c]furan-4(1H)-one 

Downstream Products

• 37841-91-1 (+)-isovelleral 

Relevant academic research and scientific papers

A novel route to the marasmane skeleton via a tandem rearrangement-cyclopropanation reaction. Total synthesis of (+)-isovelleral

A general and efficient route to the marasmane skeleton is described. Total syntheses of two simple marasmanes (35 and 37) in racemic form were achieved using a MgI2-catalyzed rearrangement-cyclopropanation reaction of trimethylsilyl enol ether 31 derived from naphthalenone 30. The reaction proceeds in high yield with complete diastereoselectivity and does not require the use of special cyclopropanation reagents. Application of this novel route to the marasmane framework was extended to the synthesis of naturally occurring (+)-isovelleral (41).

The preparation and bioactivities of (-)-isovelleral

The resolution of synthetic (±)-isovelleral (1), via chromatographic separation of the two diastereomers of the (-)-menthoxyacetic acid diester of the corresponding (±)-diol (3), yielded both enantiomers of the bioactive fungal metabolite (+)-isovelleral (1). While the antimicrobial and cytotoxic activities of the two enantiomers are comparable, natural (+)-1 is approximately 10 times more mutagenic towards Ames' tester strain TA98 than (-)-1. The two enantiomers of the cyclopropane ring isomer 2 also possess negligible mutagenicity compared to (+)-1. Both (+)-1 and (-)-1 have the same affinity for the vanilloid receptor, but significant different affinity for the dopamine D1 receptor.