메뉴 건너뛰기




Volumn , Issue 9, 2008, Pages 1460-1466

The concise synthesis of a key intermediate for the total synthesis of fumagillin, TNP-470, and ovalicin

Author keywords

Angiogenesis inhibitors; Diels alder reaction; Dihydroxylation; HIV; Syn reduction

Indexed keywords

CYCLOHEXANE; REACTION KINETICS; REDUCTION; SYNTHESIS (CHEMICAL); ZINC;

EID: 44049095593     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067030     Document Type: Article
Times cited : (5)

References (73)
  • 11
    • 44049083264 scopus 로고    scopus 로고
    • See also ref. 1d
    • (c) See also ref. 1d.
  • 26
    • 44049085430 scopus 로고    scopus 로고
    • See also ref. 3b
    • (a) See also ref. 3b.
  • 27
    • 44049096061 scopus 로고    scopus 로고
    • See also ref. 3a
    • (b) See also ref. 3a.
  • 29
    • 44049098296 scopus 로고    scopus 로고
    • PCT Int. Appl. WO 9630010, 309073
    • (a) Molina, J. M.; Derouin, F. PCT Int. Appl. WO 9630010, 1996; Chem. Abstr. 1996, 125, 309073.
    • (1996) Chem. Abstr , vol.125
    • Molina, J.M.1    Derouin, F.2
  • 34
    • 23644449722 scopus 로고    scopus 로고
    • For the total synthesis of fumagillin and the synthesis of its key intermediate fragments and some other analogues, see: (a) Camara, F, Angarita, J, Mootoo, D. R. J. Org. Chem. 2005, 70, 6870
    • For the total synthesis of fumagillin and the synthesis of its key intermediate fragments and some other analogues, see: (a) Camara, F.; Angarita, J.; Mootoo, D. R. J. Org. Chem. 2005, 70, 6870.
  • 49
    • 35948963604 scopus 로고    scopus 로고
    • For our other contributions toward the synthesis of biologically active natural products, see: b
    • For our other contributions toward the synthesis of biologically active natural products, see: (b) Yadav, J. S.; Chetia, L. Org. Lett. 2007, 9, 4587.
    • (2007) Org. Lett , vol.9 , pp. 4587
    • Yadav, J.S.1    Chetia, L.2
  • 58
    • 84980314187 scopus 로고    scopus 로고
    • Regiospecificity was determined by comparing the corresponding reactions of furfuryl alcohols with different protecting groups and studying their stereochemistry by NMR spectroscopic methods. When TBS protection was used, a mixture of isomers was formed; however, with a PMB protecting group, only one regioisomer was synthesized, see: Nelson, W. L, Allen, D. R. Heterocycl. Chem. 1972, 9, 561
    • Regiospecificity was determined by comparing the corresponding reactions of furfuryl alcohols with different protecting groups and studying their stereochemistry by NMR spectroscopic methods. When TBS protection was used, a mixture of isomers was formed; however, with a PMB protecting group, only one regioisomer was synthesized, see: Nelson, W. L.; Allen, D. R. Heterocycl. Chem. 1972, 9, 561.
  • 60
    • 44049086488 scopus 로고    scopus 로고
    • 2O. However, a prolonged reaction time with Pd/C also resulted in the saturated PMB-deprotected product.
    • 2O. However, a prolonged reaction time with Pd/C also resulted in the saturated PMB-deprotected product.
  • 67
    • 44049104869 scopus 로고    scopus 로고
    • See also ref. 14a
    • (g) See also ref. 14a.
  • 68
    • 44049084921 scopus 로고    scopus 로고
    • 2;
    • 2;
  • 70
    • 44049087752 scopus 로고    scopus 로고
    • 2O;
    • 2O;
  • 71
    • 44049106303 scopus 로고    scopus 로고
    • 2.
    • 2.
  • 72
    • 20844459615 scopus 로고    scopus 로고
    • Molecules with a similar core including an epoxide moiety were found to be biologically active, see
    • Molecules with a similar core including an epoxide moiety were found to be biologically active, see: Mazitschek, R.; Huwe, A.; Giannis, A. Org. Biomol. Chem. 2995, 3, 2150.
    • Org. Biomol. Chem , vol.2995 , Issue.3 , pp. 2150
    • Mazitschek, R.1    Huwe, A.2    Giannis, A.3
  • 73
    • 0000425224 scopus 로고    scopus 로고
    • 1,2-Asymmetric syn reduction was achieved by following a known protocol used for the stereoselective reduction of β-hydroxy ketone, see: Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233.
    • 1,2-Asymmetric syn reduction was achieved by following a known protocol used for the stereoselective reduction of β-hydroxy ketone, see: Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.