Total synthesis of optically active liverwort sesquiterpenes, trifarienols A and B, using phenylethylamine as a chiral auxiliary

Tetrahedron Asymmetry

Volumn 10, Issue 5, 1999, Pages 961-971

  Tori, Motoo ^a   Hisazumi, Kenji ^a   Wada, Tomonari ^a   Sono, Masakazu ^a   Nakashima, Katsuyuki ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

NATURAL PRODUCT; PHENETHYLAMINE; SESQUITERPENE DERIVATIVE; TRIFARIENOL A; TRIFARIENOL B; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; PRIORITY JOURNAL; RACEMIC MIXTURE; STEREOISOMERISM; STRUCTURE ANALYSIS;

EID: 0033548371     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00067-1     Document Type: Article

References (23)

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4. (c) Jabin, I.; Revial, G.; Melloul, K.; Pfau, M. Tetrahedron: Asymmetry 1997, 8, 1101-1109, and references cited therein.
5. Tori, M.; Miyake, T.; Hamaguchi, T.; Sono, M. Tetrahedron: Asymmetry 1997, 8, 2731-2738.
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7. Hashimoto, T.; Koyama, H.; Takaoka, S.; Tori, M.; Asakawa, Y. Tetrahedron Lett. 1994, 35, 4787-4788; Hashimoto, T.; Koyama, H.; Tori, M.; Takaoka, S.; Asakawa, Y. Phytochemistry 1995, 40, 171-176.
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11. Huang, H.; Forsyth, C. J. J. Org. Chem. 1995, 60, 5746-5747. Our compound 17E was geometrically pure, although the one prepared by Huang and Forsyth was a mixture of E- and Z-isomers.
12. c.f. Taishi, T.; Takechi, S.; Mori, S. Tetrahedron Lett. 1998, 39, 4347-4350.
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15. The conformation 4(F) is favored to 4(D).
16. Because 10a is racemic, there are two diastereoisomers in imine 3a. Only one half of 3a could yield 4a, while the other half remains unattached (Fig. 2). (Matrix Presented) (This is the case of the enantiomer of 3c) Figure 2.
17. Tori, M.; Uchida, N.; Sumida, A.; Furuta, H.; Asakawa, Y. J. Chem. Soc., Perkin Trans, 1 1995, 1513-1517.
18. Conditions for HPLC: Chiralcel OD-H (4.6 mmX250 mm), hexane:iPrOH=98.5:1.5, 1 mL/min.
19. Unpublished results: we have succeeded in determination of ees of several 2,2-disubstituted cyclohexanones and cyclopentanones by this methodology. Although we have reported that the ees of cyclopentanone derivatives were directly determined by chiral HPLC in Stereochemistry Abstracts in Ref. 3, this should be corresponding pentafluorophenyl esters.
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23. The melting point of the synthetic sample was ca. 20° higher than that of the natural one. This is presumably due to the fact that the natural sample includes the water in its crystal, which was indicated by the X-ray crystallography (see Ref. 4) although both crystals were made from hexane (private communication with Dr. T. Hashimoto).