Repozytorium

Lactones. Part 15: Synthesis of chiral spirolactones with a carane system-insect feeding deterrents.

Autorzy

S. Lochyński

B. Frąckowiak

Teresa Olejniczak

Zbigniew Ciunik

Czesław Wawrzeńczyk

Rok wydania

2002

Czasopismo

Tetrahedron-Asymmetry

Numer woluminu

13

Strony

1761-1767

DOI

10.1016/S0957-4166(02)00476-7

Kolekcja

Naukowa

Język

Angielski

Typ publikacji

Artykuł

Streszczenie

Starting from (+)-3-carene 1 several spirolactones with carane backbone were synthesized. δ-Hydroxy-γ-lactone 5 was obtained by acidic lactonization of a γ,δ-epoxy ester. Iodolactone 8 and bromolactone 9 were products of iodolactonization of γ,δ-unsaturated acid 7 and bromolactonization of γ,δ-unsaturated ester 3 respectively. The halo lactones were subjected to reductive dehalogenation with tributyltin hydride and dehydrohalogenation with DBU. The structures of the lactones obtained were confirmed by X-ray analysis and spectral data.

Adres publiczny

https://doi.org/10.1016/S0957-4166(02)00476-7

Strona internetowa wydawcy

http://www.elsevier.com

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