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Volumn 48, Issue 44, 2007, Pages 7747-7750

Expedient synthesis of villosin and its isomer (E)-labda-8(17),12,14-trien-15(16)-olide

Author keywords

2 Furanolates; Aldol reaction; Labdanes; Lactones; Misassigned structure; Villosin

Indexed keywords

DITERPENOID; LABDA 8(17),12,14 TRIEN 15(16) OLIDE; NATURAL PRODUCT; SCLAREOLIDE; UNCLASSIFIED DRUG; VILLOSIN;

EID: 34848870540     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.033     Document Type: Article
Times cited : (21)

References (50)
  • 19
    • 85082705352 scopus 로고
    • For alternative routes to (E)-3-(1-alkenyl)-2(5H)-furanones, see:
    • For alternative routes to (E)-3-(1-alkenyl)-2(5H)-furanones, see:. Janecki T., and Bodalski R. Synthesis (1989) 506-510
    • (1989) Synthesis , pp. 506-510
    • Janecki, T.1    Bodalski, R.2
  • 34
    • 15444378803 scopus 로고    scopus 로고
    • For an excellent review on misassigned natural products, see:
    • For an excellent review on misassigned natural products, see:. Nicolaou K.C., and Snyder S.A. Angew. Chem., Int. Ed. 44 (2005) 1012-1044
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 1012-1044
    • Nicolaou, K.C.1    Snyder, S.A.2
  • 40
    • 34848863134 scopus 로고    scopus 로고
    • For a two-step route to these alcohols from 6 and the assignment of their C-12 stereochemistry, see Ref. 9.
  • 42
    • 34848815426 scopus 로고    scopus 로고
    • note
    • 3): δ 172.6 (C-16), 149.6 (C-8), 142.7 (C-14), 137.1 (C-11), 129.7 (C-13), 120.8 (C-12), 108.6 (C-17), 69.8 (C-15), 54.9 (C-5), 62.4 (C-9), 42.5 (C-3), 41.0 (C-1), 33.8 (C-4), 39.5 (C-10), 37.0 (C-7), 23.6 (C-6), 33.8 (C-18), 19.3 (C-2), 22.2 (C-19),15.3 (C-20).
  • 43
    • 0030965153 scopus 로고    scopus 로고
    • The absolute configuration of co-existing labdanes has been established by synthesis:
    • The absolute configuration of co-existing labdanes has been established by synthesis:. Jung M., Lee S., and Yoon B. Tetrahedron Lett. 38 (1997) 2871-2874
    • (1997) Tetrahedron Lett. , vol.38 , pp. 2871-2874
    • Jung, M.1    Lee, S.2    Yoon, B.3
  • 46
    • 34848894299 scopus 로고    scopus 로고
    • note
    • +). Found: 301.2160.
  • 47
    • 34848814822 scopus 로고    scopus 로고
    • note
    • 3): δ 6.86 (dq, J = 3.2, 1.0 Hz, 1H, H-15), 6.48 (t, J = 7.2 Hz, 1H, H-12), 5.95 (d, J = 3.4 Hz, 1H, H-14), 4.83 (dd, J = 2.8, 1.4 Hz, 1H, H-17), 4.46 (dd, J = 2.6, 1.2 Hz, 1H, H-17), 2.99 (ddd, J = 17.8, 7.0, 3.2 Hz, 1H, H-11), 2.88 (ddd, J = 17.8, 11.6, 7.9 Hz, 1H, H-11), 2.40 (ddd, J = 13.0, 4.3, 2.4 Hz, 1H), 2.01 (br dt, J = 13.0, 5.5 Hz, 2H), 1.87 (br d, J = 11.5 Hz, 1H, H-9), 1.80 (dm, J = 13.0 Hz, 1H), 1.74 (dm, J = 13.0 Hz, 1H), 0.88 (s, 3H, 18-H), 0.82 (s, 3H, 19-H), 0.76 (s, 3H, 20-H).
  • 48
    • 34848855539 scopus 로고    scopus 로고
    • A similar ratio of 3/9 (ca. 4.5:1) was obtained by starting with isomerically pure 8a. Also, exposure of 8a to 0.05 equiv of DBU in dichloromethane for 5 min at rt led to a mixture containing 3, 9 and 1.
  • 50
    • 34250838591 scopus 로고    scopus 로고
    • After completion of this work, a substantially different, longer route to 1 from 5 (seven steps, 25% overall yield) was reported:
    • After completion of this work, a substantially different, longer route to 1 from 5 (seven steps, 25% overall yield) was reported:. Margaros I., and Vassilikogiannakis G. J. Org. Chem. 72 (2007) 4826-4831
    • (2007) J. Org. Chem. , vol.72 , pp. 4826-4831
    • Margaros, I.1    Vassilikogiannakis, G.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.