77480-09-2

Upstream product

• 71869-16-4 (E)-(1R,2S,10R)-1,5,8,8-Tetramethyl-bicyclo[8.1.0]undec-5-en-2-ol 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 21624-36-2 humulene 9,10-epoxide 
• 122470-66-0 Toluene-4-sulfonic acid (3E,8E)-10-cyano-10-(1-ethoxy-ethoxy)-3,6,6,9-tetramethyl-deca-3,8-dienyl ester 
• 122470-61-5 2-((E)-5-Acetoxy-3-methyl-pent-2-enyl)-2-[(E)-3-(5,5-dimethyl-[1,3]dioxan-2-yl)-but-2-enyl]-malonic acid dimethyl ester 
• 122470-63-7 2,2-Dimethyl-propionic acid (3E,8E)-9-(5,5-dimethyl-[1,3]dioxan-2-yl)-6,6-bis-iodomethyl-3-methyl-deca-3,8-dienyl ester 
• 122470-65-9 Toluene-4-sulfonic acid (3E,8E)-3,6,6,9-tetramethyl-10-oxo-deca-3,8-dienyl ester 
• 122470-62-6 (E)-6-[(E)-3-(5,5-Dimethyl-[1,3]dioxan-2-yl)-but-2-enyl]-6-hydroxymethyl-3-methyl-hept-3-ene-1,7-diol 
• 122470-64-8 (3E,8E)-9-(5,5-Dimethyl-[1,3]dioxan-2-yl)-3,6,6-trimethyl-deca-3,8-dien-1-ol 
• 62285-88-5 4-chloro-2-methyl-2-buten-1-al neopentyl acetal 
• 1030268-24-6 trimethylsulphoxonium iodide 
• 122470-59-1 (2E,7E)-2,5,5,8-Tetramethyl-cyclodeca-2,7-dienone 
• 74878-85-6 Acetic acid (E)-(1S,2S,9R,10S)-9-(tert-butyl-dimethyl-silanyloxy)-3,3,6,10-tetramethyl-bicyclo[8.1.0]undec-5-en-2-yl ester 
• 69753-93-1 bicyclohumulenediol diacetate 

Relevant academic research and scientific papers

CONFORMATIONALLY SELECTIVE TRANSANNULAR CYCLIZATION OF HUMULENE 9,10-EPOXIDE. SYNTHESIS OF THE TWO SKELETALLY DIFFERENT CYCLOHUMULANOIDS: DL-BICYCLOHUMULENONE AND DL-AFRICANOL

Two cyclohumulanoids, dl-bicyclohumulenone (4) and dl-africanol (7) were synthetized through newly developed conformationally selective transannular cyclization of humulene 9,10-epoxide (2).The epoxide 2 was converted to a bicyclohumulenediol diacetate 3a in 70percent yield by treatment with BF3.Et2O-Ac2O, while treatment of 2 with trimethylsilyl trifluoromethansulfonate gave an africen-ol (5a and 5b) in 80percent yield.The two intermediates 3a and 5a furnished the natural products 4 and 7 in 30 and 8 percent yield from 2 respectively.

Stereoselective Cyclopropanation of the 10-Membered Enone. Total Synthesis of Bicyclohumulenone

The stereoselective synthesis of bicyclohumulenone and a discusion of the diastereoselectivity of the cylopropanation based on MM2 calculations are presented.