Synthetic studies on quassinoids: total synthesis of (-)-chaparrinone, (-)-glaucarubolone, and (+)-glaucarubinone

Autor:	Paul A. Grieco, Thomas J. Fleck, Raymond S. Gross, Jon L. Collins, Eric D. Moher
Rok vydání:	1993
Předmět:	chemistry.chemical_classification Olefin fiber Bicyclic molecule Stereochemistry Chemistry Total synthesis General Chemistry Ring (chemistry) Biochemistry Catalysis Adduct chemistry.chemical_compound Colloid and Surface Chemistry Hemiacetal Enone Lactone
Zdroj:	Journal of the American Chemical Society. 115:6078-6093
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja00067a025
Popis:	The total synthesis of (-)-chaparrinone (3), (-)-glaucarubolone (4), and (+)-glaucarubinone (3) is described. The synthesis features an intermolecular Diels-Alder reaction between dienophile 6 and (E)-4-methyl-3,5-hexadienoic acid (17) in 5.0 M lithium perchlorate-ethyl acetate. Diels-Alder adduct 16 is converted via a two-step process into tetracyclic lactone 10. Inversion of configuration at C(9) and installation of a Δ 11,12 olefin in 10 provide tetracyclic lactone 19. Incorporation of the ring C functionality into 19 followed by elaboration of the ring A 1β-hydroxy-2-oxo-Δ 3,4 olefin unit and removal of the protecting groups on C(1) and C(12) hydroxyl groups affords pre-chaparrinone (41)
Databáze:	OpenAIRE
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