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Volumn 65, Issue 1, 2009, Pages 289-299

Facile access to some chiral building blocks. Synthesis of verbalactone and exophilin A

Author keywords

Carbohydrates; Chiron; Enantioselective synthesis; Epoxides; Natural products

Indexed keywords

EPOXIDE; EXOPHILIN A; LACTONE DERIVATIVE; UNCLASSIFIED DRUG; VERBALACTONE;

EID: 56949086052     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.10.050     Document Type: Article
Times cited : (33)

References (43)
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    • See, e.g.:
    • See, e.g.:
  • 6
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    • For a few existing examples of elaborating 1 into apparent chiral building blocks, see:
    • For a few existing examples of elaborating 1 into apparent chiral building blocks, see:
  • 10
    • 56949086314 scopus 로고    scopus 로고
    • Compound 2 was first reported by White (obtained by a completely different approach):
    • Compound 2 was first reported by White (obtained by a completely different approach):
  • 13
    • 0033043159 scopus 로고    scopus 로고
    • The synthesis consisted of acetylation of all the hydroxyl groups, elimination of the acetoxyl group β to the carbonyl group, catalytic hydrogenation of the C-C double bond formed by the elimination, cleavage of the remaining acetyl groups, and selective formation of the terminal acetonide
    • Pedersen C. Carbohydr. Res. 315 (1999) 192-197 The synthesis consisted of acetylation of all the hydroxyl groups, elimination of the acetoxyl group β to the carbonyl group, catalytic hydrogenation of the C-C double bond formed by the elimination, cleavage of the remaining acetyl groups, and selective formation of the terminal acetonide
    • (1999) Carbohydr. Res. , vol.315 , pp. 192-197
    • Pedersen, C.1
  • 14
    • 0037969449 scopus 로고    scopus 로고
    • For the only synthesis involving 2 (not related to the routes of Refs. 3 and 4) so far documented, see:
    • For the only synthesis involving 2 (not related to the routes of Refs. 3 and 4) so far documented, see:. Watterson M.P., Edwards A.A., Leach J.A., Smith M.D., Ichihara O., and Fleet G.W.J. Tetrahedron Lett. 44 (2003) 5853-5857
    • (2003) Tetrahedron Lett. , vol.44 , pp. 5853-5857
    • Watterson, M.P.1    Edwards, A.A.2    Leach, J.A.3    Smith, M.D.4    Ichihara, O.5    Fleet, G.W.J.6
  • 15
    • 84988087864 scopus 로고
    • Both 5 and 8 were previously synthesized from d-mannitol in 13.4% (6 steps) and 8.8% (7 steps), respectively. Chromatographic purification was required at each step therein. See:
    • Both 5 and 8 were previously synthesized from d-mannitol in 13.4% (6 steps) and 8.8% (7 steps), respectively. Chromatographic purification was required at each step therein. See:. Mulzer J., Pietschman C., Schöllhorn B., Buschmann J., and Luger P. Liebigs Ann. Chem. (1995) 1433-1439
    • (1995) Liebigs Ann. Chem. , pp. 1433-1439
    • Mulzer, J.1    Pietschman, C.2    Schöllhorn, B.3    Buschmann, J.4    Luger, P.5
  • 16
    • 56949092380 scopus 로고    scopus 로고
    • note
    • The hydrogenation was performed at 1 atm for 48 h (cf. 50 atm/12 h in Ref. 4).
  • 19
    • 56949101980 scopus 로고    scopus 로고
    • note
    • In the original method the water generated by formation of the intermediate cyclic stannylene acetals was distilled off azetropically (toluene). In this work, the water was removed by addition of activated 4 Å molecular sieves at ambient temperature.
  • 20
    • 0027771054 scopus 로고
    • see, e.g.: where J=12.0 and 16.0 Hz were reported for the cis (16Za therein) and trans (16Ea therein) isomers, respectively, of a compound with an alkenyl structure very similar to that of 10
    • see, e.g.:. Leemhuis F.M.C., Thijs L., and Zwanenburg B. J. Org. Chem. 58 (1993) 7170-7179 where J=12.0 and 16.0 Hz were reported for the cis (16Za therein) and trans (16Ea therein) isomers, respectively, of a compound with an alkenyl structure very similar to that of 10
    • (1993) J. Org. Chem. , vol.58 , pp. 7170-7179
    • Leemhuis, F.M.C.1    Thijs, L.2    Zwanenburg, B.3
  • 29
    • 9444224983 scopus 로고    scopus 로고
    • For literature precedents of cis (J=11.1 Hz) and trans (J=15.5 Hz) isomers of compounds with alkenyl structures very similar to that in 21 see: (the 5a and 5e therein, respectively)
    • For literature precedents of cis (J=11.1 Hz) and trans (J=15.5 Hz) isomers of compounds with alkenyl structures very similar to that in 21 see:. Ren H., Krasovskiy A., and Knochel P. Org. Lett. 6 (2004) 4215-4217 (the 5a and 5e therein, respectively)
    • (2004) Org. Lett. , vol.6 , pp. 4215-4217
    • Ren, H.1    Krasovskiy, A.2    Knochel, P.3
  • 33
    • 56949092782 scopus 로고    scopus 로고
    • note
    • Use of large excess of p-TsOH may lead to cleavage of the TBS protecting group.
  • 43
    • 0001527822 scopus 로고
    • For instance, they may serve as precursors for the 1,3-diol fragments broadly found in natural products; the oxo polyene macrolide family antibiotics alone already contain more than 200 members. See:
    • For instance, they may serve as precursors for the 1,3-diol fragments broadly found in natural products; the oxo polyene macrolide family antibiotics alone already contain more than 200 members. See:. Rychnovsky S.D. Chem. Rev. 95 (1995) 2021-2040
    • (1995) Chem. Rev. , vol.95 , pp. 2021-2040
    • Rychnovsky, S.D.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.