97232-48-9

Upstream product

• 116914-10-4 Widdrol-epoxid 
• 71-48-7 cobalt(III) acetate 
• 470-40-6 thujopsene 
• 34905-90-3 (1aR,2S,4aS,8aS)-2-Chloro-2,4a,8,8-tetramethyl-decahydro-cyclopropa[d]naphthalene 
• 32436-27-4 (1aR,2aS,8aS)-2a,6,6,8a-Tetramethyl-2,2a,3,4,5,6,8,8a-octahydro-1aH-1-oxa-benzo[a]cyclopropa[d]cycloheptene 
• 541-47-9 3-Methylbutenoic acid 
• 38576-60-2 senecioyl cyanide 
• 107291-63-4 Acetic acid (4aS,7S)-4a-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1,1,7-trimethyl-2,3,4,4a,5,6,7,8-octahydro-1H-benzocyclohepten-7-yl ester 
• 116913-84-9 (4aR,7S)-1,1,4a,7-Tetramethyl-2,3,4,4a,5,6,7,8-octahydro-1H-benzocycloheptene-7-carbonyl chloride 
• 470-40-6 cis-thujopsene 
• 75154-37-9 trans-2,3,4,4a,5,6,7,8,-octahydro-1,1,4a,7-tetramethyl-1H-benzocycloheptene-7-carboxylic acid 
• 116913-98-5 2,6-dimethyl-3-ethoxy-6-<2-<(trimethylsilyl)methyl>-2-butenyl>-2-cyclohexen-1-one 
• 116913-99-6 2,4-dimethyl-4-<2-<(trimethylsilyl)methyl>-2-butenyl>-3-vinyl-2-cyclohexen-1-one 
• 116914-07-9 2,3,4,4a,5,6,7,8-octahydro-1,1,4a,7-tetramethyl-1H-benzocycloheptene-6-carboxylic acid 

Downstream Products

• 94093-53-5 1,1,3-Trimethyl-3-(3,5-dihydroxy-3-methyl-pentyl)-cyclohexanol-⁽²⁾ 

Relevant academic research and scientific papers

Intramolecular [4+3] cycloadditions. Towards a synthesis of widdrol

Certain substituted alkoxyallylic sulfones were alkylated and treated with Lewis acids to produce vinylthionium ions that underwent intramolecular [4+3] cycloaddition reactions with a tethered furan. Manipulation of the cycloadduct led to the synthesis of widdrol. Other attempts to prepare the cycloadducts were made, but none were exceptionally better than the route using vinylthionium ions as intermediates. Interesting aspects of the alkylation chemistry of phenylthio-substituted alkoxyallylic sulfones are detailed as well.

REARRANGEMENT APPROACHES TO CYCLIC SKELETONS. V. FORMAL BRIDGEHEAD SUBSTITUTION OF 1-METHOXYBICYCLONON-6-EN-2-ONES AND ITS APPLICATION TO A TOTAL SYNTHESIS OF (+/-)-WIDDROL

The C-1 methoxy group of bicyclonon-6-en-2-ones is replaced by alkyl, alkenyl, and aryl groups or hydrogen with inversion of the absolute configuration via the two-step sequence consists of Grignard reaction or reduction of the carbonyl followed by

INTRAMOLECULAR ADDITIONS OF ALLYLSILANES TO CONJUGATED DIENONES. TWO SYNTHESES OF (+/-)-EPI-WIDDROL.

Two stereospecific total syntheses of epi-widdrol (1) are reported.The first synthesis features the cyclization of dienone 3a to construct bicyclic adduct 4a which is converted to epi-widdrol using conventional procedures.A second synthesis exploits the cyclization of dienone 17 to prepare functionalized bicycloundecene 18, which is converted to a known epi-widdrol precursor.

A TOTAL SYNTHESIS OF (+/-)-WIDDROL. SYNTHETIC APPLICATION OF THE FORMAL BRIDGEHEAD SUBSTITUTION OF 1-METHOXYBICYCLONON-6-EN-2-ONES WITH ALKYL GROUPS

The fused-ring sesquiterpene (+/-)-widdrol has been prepared stereospecifically utilizing the characteristic reactions of the bridged polycyclic compounds derived from 1-methoxy-5-methylbicyclonon-6-en-2-one.

Oxidation of Thujopsene with Lead Tetraacetate

We investigated the oxidation of thujopsene with lead tetraacetate.In the hydrolysis product, two new sesquiterpenoids were found to be afforded: 6α, 10, 10-trimethyl-4β-acetyltricyclo1,3>decane and its C(4)-stereoisomer.