84104-87-0

Basic information

• Product Name: 2,3-Phenanthrenediol, 4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-1-(1-methylethyl)-, (4bS,8aS)-
• Synonyms: 2,3-Phenanthrenediol, 4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-1-(1-methylethyl)-, (4bS,8aS)-
• CAS NO: 84104-87-0
• Molecular Formula: C₂₀H₃₀O₂
• Molecular Weight: 0
• Mol File: 84104-87-0.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3-Phenanthrenediol, 4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-1-(1-methylethyl)-, (4bS,8aS)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Phenanthrenediol, 4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-1-(1-methylethyl)-, (4bS,8aS)-(84104-87-0)
• EPA Substance Registry System: 2,3-Phenanthrenediol, 4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-1-(1-methylethyl)-, (4bS,8aS)-(84104-87-0)

Safety Data

• Hazardous Substances Data: 84104-87-0(Hazardous Substances Data)

Upstream product

• 51847-85-9 13-methoxytotara-8,11,13-trien-12-ol 
• 1089322-09-7 13-methoxytotara-8,11,13-triene 
• 84104-94-9 12-bromo-13-methoxytotara-8,11,13-triene 
• 51905-93-2 12,13-dimethoxy-14-isopropylpodocarpa-8,11,13-triene 
• 51847-85-9 13-methoxytotara-8,11,13-trien-12-ol 
• 51905-87-4 12-aminototara-8,11,13-trien-13-ol 
• 84104-91-6 13-methoxytotara-8,11,13-trien-12-yl acetate 
• 84104-90-5 12-acetyl-13-methoxytotara-8,11,13-triene 
• 84104-94-9 12-bromo-13-methoxytotara-8,11,13-triene 
• 15340-83-7 13-methoxy-totara-8,11,13-triene 
• 117451-40-8 12,13-dimethoxy-14-(1-formylethyl)-podocarpa-8,11,13-triene 
• 117451-45-3 12,13-dimethoxy-14-(1-methallyl)-podocarpa-8,11,13-triene 
• 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 

Downstream Products

• 142791-48-8 12-benzyloxytotara-6,8,11,13-tetraen-13-ol 
• 142791-49-9 12,13-dibenzyloxytotara-6,8,11,13-tetraene 
• 84104-88-1 totara-8,11,13-triene-12,13-diol dibenzoate 
• 142791-50-2 9α-benzyl-12-benzyloxytotara-8(14),11-dien-13-one 

Relevant articles and documents

Synthesis of totarane diterpenes: Totarol, maytenoquinone, 6-deoxymaytenoquinone and 8,11,13-totaratriene-12,13-diol

The syntheses of four totarane diterpenes - totarol, 8,11,13-totaratriene- 12,13-diol, 6-deoxymaytenoquinone and maytenoquinone - are described. Totarol was synthesized via cyclization of a modified polyene. 8,11,13-Totaratriene-12, 13-diol was prepared from natural totarol by ortho-oxidation with mCBPO (m-chlorobenzoyl peroxide). Maytenoquinone and 6-deoxymaytenoquinone were synthesized from 8,11,13-totaratriene-12,13-diol. 1H-NMR analysis showed that tautomeric isomerization between 6-deoxymaytenoquinone (2-hydroxy-4-quinone methide) and the ortho-quinone was very slow.

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.