56012-88-5

Upstream product

• 106536-82-7 (R)-3-Methyl-2-((1R,3aS,7aR)-3a-methyl-7-methylene-3-oxo-octahydro-inden-1-yl)-butyric acid 
• 106536-82-7 (S)-3-Methyl-2-((1R,3aS,7aR)-3a-methyl-7-methylene-3-oxo-octahydro-inden-1-yl)-butyric acid 
• 106536-87-2 [(S)-2-Methyl-1-((1R,3aR,7aR)-3a-methyl-7-methylene-octahydro-inden-1-yl)-propyl]-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 106536-85-0 (S)-3-Methyl-2-((1R,3aR,7aR)-3a-methyl-7-methylene-octahydro-inden-1-yl)-butyryl chloride 
• 106536-84-9 (S)-3-Methyl-2-((1R,3aR,7aR)-3a-methyl-7-methylene-octahydro-inden-1-yl)-butyric acid 
• 106536-78-1 Trimethyl-((3aR,7aS)-7a-methyl-4-methylene-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yloxy)-silane 
• 106536-79-2 (3aR,7aS)-2-Bromo-7a-methyl-4-methylene-octahydro-inden-1-one 
• 106536-81-6 (3aR,7aS)-7a-Methyl-4-methylene-3a,4,5,6,7,7a-hexahydro-inden-1-one 
• 92490-61-4 3-<2-(5-chloro-1-pentenyl)>-2-methylcyclopentanone 
• 92490-72-7 cis-6-methyl-2-methylenebicyclo<4.3.0>nonan-7-one 
• 106536-87-2 [(S)-2-Methyl-1-((1R,3aR,7aR)-3a-methyl-7-methylene-octahydro-inden-1-yl)-propyl]-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 106536-82-7 (S)-3-Methyl-2-((1R,3aS,7aR)-3a-methyl-7-methylene-3-oxo-octahydro-inden-1-yl)-butyric acid 
• 106536-85-0 (S)-3-Methyl-2-((1R,3aR,7aR)-3a-methyl-7-methylene-octahydro-inden-1-yl)-butyryl chloride 
• 106536-84-9 (S)-3-Methyl-2-((1R,3aR,7aR)-3a-methyl-7-methylene-octahydro-inden-1-yl)-butyric acid 

Downstream Products

• 53822-96-1 (+/-)-axisonitrile 
• 53822-96-1 (+/-)-axisonitrile-1 

Relevant academic research and scientific papers

Total syntheses of (±)-axamide-1 and (±)-axisonitrile-1 via 6-Exo-dig radical cyclization

Total syntheses of (±)-axamide-1 (1) and (±)-axisonitrile-1 (2) were accomplished by using the α-carbonyl radical cyclization as the key step. Thienylcyanocuprate 24 mediated conjugated addition of 5-(trimethylsilyl)-4-pentynylmagnesium chloride (23) to 3

Synthesis of carbocycles via intramolecular conjugate additions: Total syntheses of axane sesquiterpenoids

Syntheses of (±)-axamide-1 (2) and (±)-axisonitrile-1 (1) are described. The syntheses require 12 steps and 13 steps, respectively, from vinylogous ester 8 and feature the diastereoselective cyclization of unsaturated ester 7 to perhydroindan 5. Some interesting reactions of the organometallic derived from [(trimethylsilyl)methyl]magnesium chloride and cerium trichloride are also described.

METHYLENECYCLOHEXANE ANNULATION. TOTAL SYNTHESIS OF (+/-)-AXAMIDE-1, (+/-)-AXISONITRILE-1, AND THE CORRESPONDING C-10 EPIMERS

Conjugate addition of 2-(5-chloro-1-pentenyl)magnesium bromide (12) to 2-methyl-2-cyclopenten-1-one (6), followed by intramolecular alkylation of the resultant product, afforded (85percent) the bicyclic ketone 7, which was transformed (77percent) into the enone 16.Titanium tetrachloride-catalyzed conjugate addition of 3-methyl-1,1-bis(trimethylsiloxy)-1-butene to 16 gave (93percent) a 3:2 mixture of the keto acids 20 and 21, which were separated.Compound 20, the stereochemistry of wich was confirmed by a single-crystal X-ray analysis, was converted into (+/-)-axamide-1 (1) and (+/-)-axisonitrile-1 (2), while 21 was transformed into the corresponding C-10 epimers 8 and 9, respectively.

Total syntheses of the sesquiterpenoids (+/-)-axamide-1, (+/-)-axisonitrile-1, and the corresponding C-10 epimers

Total syntheses of (+/-)-axamide-1 (1), (+/-)-axisonitrile-1 (2), and the corresponding C-10 epimers 16 and 17 are described.The key steps of the synthetic sequence involve methylenecyclohexane annulation of 2-methyl-2-cyclopenten-1-one and TiCl4-catalyzed conjugate addition of 3-methyl-1,1-bis(trimethylsiloxy)-1-butene to the bicyclic enone 8.