Non-Macrocyclic Trichothecenes, Part 2 (1)
A total of 182 trichothecenes, based on the trichothecane skeleton (1 ), have now been isolated from natural sources. They are made up of 113 non-macrocyclic and 69 macrocyclic compounds (2 ). Thirty-four more naturally-occurring trichothecenes have there
- PDF / 6,163,302 Bytes
- 70 Pages / 439.37 x 666.14 pts Page_size
- 56 Downloads / 166 Views
Introduction and Nomenclature ............................................... 2 Naturally Occurring Compounds .............................................. 3 Unnatural Trichothecenes ................................................... 12 Chemistry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 13 4.1. Ethylenic Double Bonds ................................................. 14 4.1.1. Isomerization . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 14 4.1.2. Catalytic Reduction ............................................... 15 4.1.3. Electrophilic Addition Reactions ................................... 15 4.1.3.1. Epoxidation of 9-Enes ...................................... 15 4.1.3.2. Epoxidation of 12-Enes ..................................... 15 4.1.3.3. Epoxidation of 7-Enes ...................................... 15 4.1.3.4. Hydroxylation ............................................. 16 4.1.3.5. Bromination .............................................. 16 4.1.3.6. Carbene Addition .......................................... 17 4.1.4. Reactions at the (X-Carbon Atom ................................... 17 4.1.5. Ozonolysis ....................................................... 17 4.2. Hydroxyl Groups ....................................................... 18 4.2.1. Regioselective Esterification and Etherification, and Regeneration of the Hydroxyl Function. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 18 4.2.1.1. Verrucarol ................................................ 18 4.2.1.2. Scirpenetriol............................................... 18 4.2.1.3. T-2 Tetrao!. ............................................... 19 4.2.1.4. Vomitoxin and Nivalenol ................................... 20 4.2.1.5. 12-01s .................................................... 21 4.2.2. Regioselective Oxidation ........................................... 21 4.2.2.1. 8-01s ..................................................... 21 4.2.2.2. 15-01s .................................................... 21
* Reviewing the literature published between January 1987 and December 1995. W. Herz et al. (eds.), Progress in the Chemistry of Organic Natural Products © Springer-Verlag/Wien 1996
2
1. F.
GROVE
4.2.2.3. 3-01s ..................................................... 4.2.2.4. 4-01s ..................................................... 4.2.2.5. 12-01s .................................................... 4.2.3. Deoxygenation .................................................... 4.2.4. Nucleophilic Substitution .......................................... 4.3. Keto Groups ........................................................... 4.3.1. Derivative Formation ............................................. 4.3.2. Regio- and Stereo-Selective Reduction .............................. 4.3.3. Nucleophilic Addition Reactions ................................... 4.3.3.1. Phosphorus Y
Data Loading...
