24406-03-9

Upstream product

• 91292-06-7 3,8-dimethyl-5α-isopropyl-3-phenylthio-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one 
• 80485-50-3 8a-hydroxy-5α-isopropyl-8-methyl-3-phenylthioperhydronaphthalen-2-one 
• 74-88-4 methyl iodide 
• 91292-05-6 5α-isopropyl-8-methyl-3-phenylthio-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one 
• 87226-70-8 cis-7-methoxycalamenene 
• 87226-67-3 8-Isopropyl-3-methoxy-5-methyl-7,8-dihydro-naphthalene-2-carbaldehyde 
• 87226-71-9 β-4-isopropyl-β-1-methyl-6-formyl-7-methoxy-1-tetralol 
• 113706-58-4 5-Isopropenyl-3,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ol 

Downstream Products

• 2954-53-2 2-3,5-Dinitrobenzoat 

Relevant academic research and scientific papers

Total Synthesis and Antibiotic Properties of Amino-Functionalized Aromatic Terpenoids Related to Erogorgiaene and the Pseudopterosins

Following a concept recently introduced by Hergenrother,[6] the present study addresses the question of whether certain antimicrobially active aromatic (marine) natural products can be converted into more potent broad-spectrum antibiotics by introducing an aminoalkyl side chain. To this end, phenolic mono- and sesquiterpenoids (incl. carvacrol, xanthorrhizol, and 7-hydroxycalamene) as well as the diterpenes 7-hydroxyerogorgiaene and 9-deoxypseudopterosin A were converted into amino-functionalized analogs that display either an amino-methyl or a 2-amino-ethoxy substituent in place of (or next to) the OH group. This was achieved either by Pd-catalyzed nitromethylation/reduction of the aryltriflates, by O-alkylation of the phenols with bromoacetonitrile and subsequent reduction, or by ortho-hydroxymethylation/amination. During the study, an efficient enantioselective total synthesis of 7-hydroxyerogorgiaene (8 steps, 29 % overall yield) and 9-deoxypseudopterosin A (9 steps, 30 % overall yield) was elaborated using an asymmetric cobalt-catalyzed hydrovinylation (91 % ee) of 3-methoxy-4-methyl-styrene as the chirogenic step. Other important C?C bond forming steps include a Pd-catalyzed Suzuki cross-coupling and diastereoselective Lewis acid-mediated cyclization reactions. A total of 16 amino derivatives of natural products were prepared and subsequently tested for their antibacterial properties. Some of the diterpene-derived amines showed high efficacy, not only against Gram-positive (S. aureus SG511, S. aureus HG003, B. subtilis 168; MIC=0.5 to 2 μg/ml), but also against Gram-negative bacterial strains (E. coli K12; E. coli I-11276b; MIC=8 to 32 μg/ml). This clearly supported the underlying working hypothesis.

STEREO- AND REGIOSELECTIVE SYNTHESIS OF HYDROXYCALAMENENES VIA (ARENE)TRICARBONYL CHROMIUM COMPLEXES

Stereoisomers of 7- and 8-hydroxycalamenenes were synthesized stereo- and regioselectively via (arene)tricarbonyl chromium complexes.

Reactions of 3-Phenylthiobut-3-en-2-one. Part 4. Novel and Efficient Synthesis of 7-hydroxycalamenene, Ferruginol, and D-Homoestrone

The annelation reaction of 3-phenylthiobut-3-en-2-one with carvomenthone (1) gives 8a-hydroxy-4α-isopropyl-1-methyl-6-phenylthioperhydronaphthalen-7-one (2), which is converted into 7-hydroxycalamenene (4) by subsequent dehydration, methylation, and aroma