Protecting group free enantiospecific total syntheses of structurally diverse natural products of the tetrahydrocannabinoid family
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چکیده
منابع مشابه
Protecting group free enantiospecific total syntheses of structurally diverse natural products of the tetrahydrocannabinoid family.
A simple, highly diastereoselective, Lewis acid catalyzed Friedel-Crafts coupling of a cyclic allylic alcohol with resorcinol derivatives has been developed. The method was applied for the enantiospecific total syntheses of structurally diverse natural products such as machaeriol-D, Δ(8)-THC, Δ(9)-THC, epi-perrottetinene and their analogues. Synthesis of both natural products and their enantiom...
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Two convenient methodologies have beendescribed for the enantiospecific synthesis of (–)-valeranone 1. The hydrindanone 12, obtained from the readily andabundantly available monoterpene (R)-carvone,has been converted into the ketoaldehyde 16via the alkene 15b. In anotherdirection the lactone 18, obtainedfrom the hydrindanone 12, has beenelaborated into the ketoaldehyde 16employing two methodolo...
متن کاملThe total syntheses of basiliolide C, epi-basiliolide C, and protecting-group-free total syntheses of transtaganolides C and D.
The total syntheses of basiliolide C and previously unreported epi-basiliolide C are achieved by an Ireland-Claisen/Diels-Alder cascade. The development of a palladium catalyzed cross-coupling of methoxy alkynyl zinc reagents allows for the protecting-group-free syntheses of transtaganolides C and D. Syntheses of transtaganolides C and D are accomplished in a single operation to generate three ...
متن کاملTotal syntheses of natural products containing spirocarbocycles.
The structures of natural products from a variety of sources contain spirocycles, two rings that share a common atom. The spiro motif is finding increasing inclusion in drug candidates, and as a structural component in several promising classes of chiral ligands used in asymmetric synthesis. Total syntheses of products containing all-carbon spirocycles feature several common methods of ring clo...
متن کاملThe catalytic enantioselective, protecting group-free total synthesis of (+)-dichroanone.
Herein we report the first enantioselective total synthesis of (+)-dichroanone, confirming the absolute configuration of the natural product. This protecting group-free route features the first application of our enantioselective Tsuji allylation in the context of a natural product total synthesis. Additionally, this 11-step preparation of the molecule from commercial material features a novel ...
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ژورنال
عنوان ژورنال: Chemical Communications
سال: 2015
ISSN: 1359-7345,1364-548X
DOI: 10.1039/c4cc08562k