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Volumn 127, Issue 40, 2005, Pages 13813-13815

Enantioselective total synthesis of isoedunol and β-araneosene featuring unconventional strategy and methodology

Author keywords

[No Author keywords available]

Indexed keywords

BETA ARANEOSENE; CLAVIROLIDE; CLAVULACTONE; CYTOTOXIC AGENT; ISOEDUNOL; LACTONE; UNCLASSIFIED DRUG;

EID: 26444455993     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja055137+     Document Type: Article
Times cited : (53)

References (33)
  • 1
    • 26444567972 scopus 로고
    • Ph.D. Thesis, Eidenøssischen Technischen Hochschule (ETH) Zürich, No. 5578
    • Borschberg, H.-J. Ph.D. Thesis, Eidenøssischen Technischen Hochschule (ETH) Zürich, No. 5578, 1975.
    • (1975)
    • Borschberg, H.-J.1
  • 9
    • 26444472892 scopus 로고    scopus 로고
    • note
    • (c) See ref 2.
  • 12
    • 26444511837 scopus 로고    scopus 로고
    • note
    • See the Supporting Information for method of preparation. Note that compounds 7-11 in Scheme 1 were prepared as an inconsequential mixture of acetonide diastereomers so that rac-5 could serve as starting material.
  • 13
    • 0000093325 scopus 로고
    • Diastereoselective alkylation of chiral enolates derived from α-heterosubstituted carboxylic acids: (a) Seebach, D.; Naef, R. Helv. Chim. Acta 1981, 64, 2704-2708.
    • (1981) Helv. Chim. Acta , vol.64 , pp. 2704-2708
    • Seebach, D.1    Naef, R.2
  • 17
    • 0041340694 scopus 로고    scopus 로고
    • For recent reviews on the application of titanacyclopropane reagents, see: (a) Kulinkovich, O. G. Chem. Rev. 2003, 103, 2597-2632.
    • (2003) Chem. Rev. , vol.103 , pp. 2597-2632
    • Kulinkovich, O.G.1
  • 23
    • 0346787791 scopus 로고    scopus 로고
    • (a) Kagan, H. B. Tetrahedron 2003, 59, 10351-10372.
    • (2003) Tetrahedron , vol.59 , pp. 10351-10372
    • Kagan, H.B.1
  • 26
    • 0000587441 scopus 로고    scopus 로고
    • For cyclopropanation of secondary α-hydroxy, α-alkoxy, and α-amino ester substrates, respectively, see: (a) Cho, S. Y.; Cha, J. K. Org. Lett. 2000, 2, 1337-1340.
    • (2000) Org. Lett. , vol.2 , pp. 1337-1340
    • Cho, S.Y.1    Cha, J.K.2
  • 29
    • 0002561992 scopus 로고    scopus 로고
    • Alternative methods involve Sharpless asymmetric epoxidation and asymmetric dihydroxylation of the cyclopropylidene group, followed by ring expansion. Unfortunately, an allylic hydroxyl group is a requirement for high enantioselectivity in the epoxidation event, and the cinchona-catalyzed asymmetric dihydroxylation of a tetrasubstituted cyclopropylidene olefin proceeds with only modest selectivity. For details, see: (a) Nemoto, H.; Fukumoto, K. Synlett 1997, 863-875.
    • (1997) Synlett , pp. 863-875
    • Nemoto, H.1    Fukumoto, K.2
  • 32
    • 26444548816 scopus 로고    scopus 로고
    • Ph.D. Thesis, Harvard University
    • Racemic 11 had previously been prepared by the spiroannulation method of Trost from the corresponding methyl ketone. For details, see: Thomas W. Lee, Ph.D. Thesis, Harvard University, 2001.
    • (2001)
    • Lee, T.W.1
  • 33
    • 26444445873 scopus 로고    scopus 로고
    • note
    • For a review on other synthetic approaches to dolabellanes, see ref 4.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.