Synthesis and absolute stereochemistry of the acyl moiety of quillajasaponins

Tetrahedron Letters

Volumn 41, Issue 5, 2000, Pages 717-719

  Zhu, Xiangming ^a   Yu, Biao ^a   Hui, Yongzheng ^a   Higuchi, Ryuichi ^b   Kusano, Takanori ^b   Miyamoto, Tomofumi ^b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

IMMUNOLOGICAL ADJUVANT; OCTANOIC ACID DERIVATIVE; SAPONIN DERIVATIVE;

ARTICLE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034728163     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02124-3     Document Type: Article

References (19)

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14. 8 regardless of the β-chirality occurring in the aldehyde substrate (7).
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16. 10 did not lead to the desired δ lactone 12(6S).
17. 3: 172.1100, found: 172.1120.
18. 1H NMR spectra of 12(6S) and 12(6R), the differences between the signals for the protons adjacent to the stereogenic center C-6 are observable: (i) the signal for H-5 of 12(6S) shows ddd peak with J=3.0, 4.1, 12.1 Hz, while that for 12(6R) shows ddd peak with J=2.9, 5.7, 12.0 Hz; (ii) the signal for one of the H-7 of 12(6S) appears at 1.57 ppm, while that for 12(6R) moves downfield to 1.78 ppm.
19. 8,9.