(+)-Podocarpic Acid as Chiral Template in the Synthesis of Aphidicolane, Stemodane and Stemarane Diterpenoids †
| Autor: | Francesca Leonelli, Luisa Maria Migneco, Rinaldo Marini Bettolo, Angela La Bella |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
synthesis
Stereochemistry Pharmaceutical Science Review 010402 general chemistry aphidicolin 01 natural sciences Analytical Chemistry Calceolariaceae lcsh:QD241-441 Aphidicolin podocarpic acid stemarin stemodin organic chemistry Podocarpic acid lcsh:Organic chemistry Drug Discovery Physical and Theoretical Chemistry 010405 organic chemistry Chemistry Model study Organic Chemistry Absolute configuration Plantaginaceae Terpenoid 0104 chemical sciences Chemistry (miscellaneous) Abietanes Molecular Medicine |
| Zdroj: | Molecules, Vol 21, Iss 9, p 1197 (2016) Molecules |
| ISSN: | 1420-3049 |
| Popis: | In this review the synthetic work in the field of aphidicolane, stemodane and stemarane diterpenoids, in which readily available (+)-podocarpic acid (4) was used as chiral template for the construction of their polycyclic structures, is described as it developed along the years. In the frame of this work (+)-podocarpic acid (4) was a very useful tool in a model study leading to the syntheses of tetracyclic ketones 7 and 8, models of key intermediates 5a and 6 in the syntheses of (+)-aphidicolin (1) and (+)-stemodin (2a), respectively. (+)-Podocarpic acid (4) was also converted into (+)-2-deoxystemodinone (2d), allowing confirmation of the stemodane diterpenoids absolute configuration, into (+)-aphidicol-15-ene (36) and into Stemodia chilensis tetracyclic diterpenoid (+)-19-acetoxystemodan-12-ol (2f), allowing confirmation of its structure. (+)-Podocarpic acid (4) was then extensively used in the work which led to the synthesis of (+)-stemar-13-ene (57) and (+)-18-deoxystemarin (3b). Finally, (+)-4 was converted into (+)-2-deoxyoryzalexin S (66), which made it possible to demonstrate that the structure of (+)-66 could not be attributed to a Chilean Calceolaria isolated diterpenoid to which this structure had been assigned. |
| Databáze: | OpenAIRE |
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