Total synthesis of (+)-epiepoformin and (-)-phyllostine

Tetrahedron

Volumn 59, Issue 51, 2003, Pages 10159-10164

  Okamura, Hiroaki ^a   Shimizu, Hideki ^b   Yamashita, Naomi ^a,c   Iwagawa, Tetsuo ^a   Nakatani, Munehiro ^a  

^a KAGOSHIMA UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

^c Panapharm Laboratories Co Ltd   (Japan)

Author keywords

Diels Alder reaction; Epiepoformin; Phyllostine; Theobroxide; Total synthesis

Indexed keywords

CYCLOHEXANE OXIDE; EPIEPOFORMIN; OXIDE; PHYLLOSTINE; PYRONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHIRALITY; DIELS ALDER REACTION; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

BETULACEAE;

EID: 0344064777     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.10.065     Document Type: Article

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32. 4,6a,b but we isolated pure phyllostine as a yellowish oil, which agrees with the calculated values of elemental analysis. The product is relatively unstable and after 24 h at room temperature, it changed into pale brown solid that no longer satisfied the elemental analysis.
33. Since the overlapped signal at 54.0 ppm corresponding to the epoxy carbons, only five signals were observed. The signal intensity at 54.0 ppm was higher than its methylene carbon at 59.2 ppm.