51847-85-9

Upstream product

• 117451-40-8 12,13-dimethoxy-14-(1-formylethyl)-podocarpa-8,11,13-triene 
• 10064-08-1 (+)-(5S,10S)-12-methoxypodocarpa-8,11,13-triene 
• 79577-89-2 13-hydroxy-12-methoxy-13-deisopropyldehydroabietane 
• 71596-68-4 (2-Isopropyl-3,4-dimethoxy-phenyl)-methanol 
• 63512-92-5 3,4-Dimethoxy-2-isopropylbenzylchlorid 
• 71596-67-3 3.4-dimethoxy-2-isopropyl-benzoic acid methyl ester 
• 117451-39-5 12-methoxy-13-hydroxy-14-(1-methallyl)-podocarpa-8,11,13-triene 
• 117451-38-4 12-methoxy-13-but-2-enyloxypodocarpa-8,11,13-triene 
• 117451-37-3 Formic acid (4bS,8aS)-3-methoxy-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-2-yl ester 
• 85852-97-7 12-methoxypodocarpa-8,11,13-triene-13-carbaldehyde 
• 85852-96-6 12-hydroxypodocarpa-8,11,13-triene-13-carbaldehyde 
• 84104-92-7 12-nitro-13-methoxytotara-8,11,13-triene 
• 84104-89-2 12-nitrototara-8,11,13-trien-13-ol 
• 511-15-9 trans-totarol 

Downstream Products

• 84104-87-0 (4aS,10aS)-1,2,3,4,4a,9,10,10a-octahydro-6,7-dihydroxy-8-isopropyl-1,1,1,4a-trimethylphenanthrene 
• 84104-88-1 totara-8,11,13-triene-12,13-diol dibenzoate 
• 84104-87-0 8-Isopropyl-podocarpan-6,7-diol 
• 142791-50-2 9α-benzyl-12-benzyloxytotara-8(14),11-dien-13-one 
• 142791-49-9 12,13-dibenzyloxytotara-6,8,11,13-tetraene 
• 142791-48-8 12-benzyloxytotara-6,8,11,13-tetraen-13-ol 

Relevant academic research and scientific papers

Regioselective hydroxylation of (η6-arene)tricarbonylchromium(0) complexes of diterpenoids

A novel procedure has been developed for the regioselective hydroxylation of ring-C aromatic diterpenoids via their (η6-arene)tricarbonylchromium(0) complexes.Lithiation-cupration-oxidation gives good yields from methoxyarene complexes having an unhindered ortho position.

The synthesis and antibacterial activity of totarol derivatives. Part 2: Modifications at C-12 and O-13

Alterations of the C-12 and C-13 aromatic ring substituents of totarol (1) afforded the series of derivatives 2-14, and introduction of substituents at C-12 gave exclusively 2a-14a. The majority of these analogues were tested in vitro against the following organisms: β-lactamase-positive and high level gentamycin-resistant Enterococcus faecalis, penicillin-resistant Streptococcus pneumoniae, methicillin-resistant Staphylococcus aureus (MRSA), and multiresistant Klebsiella pneumoniae. The results were evaluated in terms of structure-activity relationship which reveals that: (a) the phenolic moiety at C-13, in general, is essential for antibacterial activity at 32 μg/mL against Gram-positive species, and (b) derivatization at C-12 has an undesirable effect on the antibacterial activity of this class of compounds, while (c) all compounds tested are ineffective against the Gram-negative Klebsiella pneumoniae. Copyright (C) 2000 Elsevier Science Ltd.

Phenolic Oxidations of Totarol

Methods for the direct oxidation of the C 12 position of totarol (1) or its methyl ether (4) have been examined.Treatment of (1) with benzeneseleninic anhydride gave the 9-hydroxy dienone (16) which on ozonolysis afforded the spiro butenolide (21), formed via the ozonide (22).The rearranged ether (18) was obtained from one oxidation with benzeneseleninic anhydride.Mercuriation of totarol and totaryl methyl ether gave the mercuriochlorides (5) and (7) but attempts to form the methoxy acetate (6) from (7) by boronation/oxidation and acetylation were unsuccessful.Treatment of totaryl methyl ether (4) with thallium(III) trifluoroacetate gave dienone 14- and 9-trifluoroacetates (25) and (17).Reaction of the (η6-arene)tricarbonylchromium(0) complexes (28) and (29) of (4) with lithioacetonitrile gave the 7α-alcohol (30) but reaction with t-butyllithium and then with copper(I) bromide/dimethyl sulfide and MoOPH gave the methoxyphenol (12) in 66percent yield.

Synthesis of maytenoquinone

A synthesis of maytenoquinone (11) from natural podocarpic acid (1) is described.