53823-07-7

Upstream product

• 78173-24-7 (1aS,4aS,7aS,7bR)-3,3,7b-Trimethyl-5-methylene-decahydro-cyclopropa[e]azulen-4a-ol 
• 104166-08-7 (1R,7S)-1,5,5-Trimethyl-bicyclo[5.1.0]octan-2-one 
• 107770-60-5 1-((1R,7S)-1,5,5-Trimethyl-bicyclo[5.1.0]oct-2-en-3-yl)-ethanone 
• 107770-67-2 (1aS,4aS,7aS,7bR)-3,3,5,7b-Tetramethyl-1,1a,2,3,4,7,7a,7b-octahydro-cyclopropa[e]azulen-4a-ol 
• 132034-07-2 (1S,2S,8S)-2-(4'-butenyl)-1,5,5-trimethyl-bicyclo<5.1.0>-3-octanone 
• 107770-62-7 ethyl (1R^*,2R^*,7S^*)-3-<(E)-ethylidene>-1,5,5-trimethylbicyclo<5.1.0>octane-2-acetate 
• 107770-63-8 (1aR^*,7aR^*,7bS^*)-1,1a,2,3,4,7,7a,7b-octahydro-3,3,5,7b-tetramethyl-6H-cyclopropazulen-6-one 
• 107770-64-9 (1aR^*,6R^*,7aR^*,7bS^*)-1a,2,3,4,6,7,7a,7b-octahydro-3,3,5,7b-tetramethyl-1H-cyclopropazulen-6-ol 
• 107770-66-1 (1aR^*,4aS^*,5R^*,6R^*,7aR^*,7bS^*)-4a,5-epoxydecahydro-3,3,5,7b-tetramethyl-1H-cyclopropazulen-6-ol 
• 107770-61-6 (R)-1-((1R,7S)-1,5,5-Trimethyl-bicyclo[5.1.0]oct-2-en-3-yl)-ethanol 
• 107770-61-6 (S)-1-((1R,7S)-1,5,5-Trimethyl-bicyclo[5.1.0]oct-2-en-3-yl)-ethanol 
• 107770-58-1 methyl (1R^*,3S^*,7S^*)-1,5,5-trimethyl-2-oxobicyclo<5.1.0>octane-3-carboxylate 
• 107770-47-8 (1R^*,2R^*,7S^*)-3-<(E)-ethylidene>-1,5,5-trimethylbicyclo<5.1.0>octane-2-acetic acid 
• 107770-59-2 methyl cis-1,5,5-trimethylbicyclo<5.1.0>oct-2-ene-3-carboxylate 

Downstream Products

• 58542-75-9 (+)-Dactylol 

Relevant academic research and scientific papers

TOTAL SYNTHESIS OF AFRICANOL

The first total synthesis of africanol has been achieved in 18 steps from ketone 5 by a route that for the most part is highly stereocontrolled.

A short total synthesis of (±)-isoafricanol and two of its isomers

The syntheses of (±)-isoafricanol and two of its isomers were achieved from 2,5,5-trimethylcyclohex-2-en-1-ol. The key step was a photoreductive radical cyclisation of an unsaturated ketone.

Synthetic Approach for (+)-Africanol

Synteses of (+)-africanol (1) and (+)-isoafricanol (2) were attempted by reductive radical cyclization of (1S,2S,8S)-2-(4'-butenyl)-1,5,5-trimethyl-bicyclo-3-octanone derived from (1R,2S,4S,8S)-4-alkoxy-1,6,6-trimethyl-tricyclo2,4>nonane.This cyclization gave (+)-1 and (+)-2 as minor components, together with trans fused epimers as major components.

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.