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Volumn , Issue 8, 2008, Pages 1202-1204

Synthesis of bistramide A and analogues, part 1: Stereoselective access to normethyl tetrahydropyran subunit

Author keywords

Bistramide A; Cross metathesis reaction; Intramolecular oxa Michael reaction; Normethyl; Sharpless epoxidation

Indexed keywords

BISTRAMIDE A; NATURAL PRODUCT; TETRAHYDROPYRAN DERIVATIVE;

EID: 44349144401     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1072714     Document Type: Article
Times cited : (18)

References (39)
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    • 44349187061 scopus 로고    scopus 로고
    • -1.
    • -1.
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    • 3).
    • 3).
  • 26
    • 44349112677 scopus 로고    scopus 로고
    • 3): δ = 25.1, 33.9, 37.4, 38.5, 61.7, 72.0, 114.9, 138.9.
    • 3): δ = 25.1, 33.9, 37.4, 38.5, 61.7, 72.0, 114.9, 138.9.
  • 27
    • 44349137185 scopus 로고    scopus 로고
    • -1.
    • -1.
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    • 44349145406 scopus 로고    scopus 로고
    • Compound 8 (trans isomer, α]D 20 -43.1 (c, 1, CHCl3, 1H NMR (300 MHz, CDCl3, δ, 0.04 (s, 6 H, 2 x Me, 0.88 (s, 9 H, 3 x Me, 1.24-1.48 (m, 2 H, 1.51-1.70 (m, 5 H, 1.90-2.02 (m, 1 H, 2.41 (dd, J, 5.5, 14.7 Hz, 1 H, 2.59 (dd, J, 8.3, 14.7 Hz, 1 H, 3.60-3.67 (m, 2 H, 3.67 (s, 3 H, 3.89-3.94 (m, 1 H, 4.10-4.16 (m, 1 H, 13C NMR (75 MHz, CDCl3, δ, 5.0 (2 x C, 18.6, 18.8, 26.3 (3 x C, 29.9, 30.4, 35.9, 39.9, 51.9, 60.2, 67.9, 69.1, 172.3. IR: 2928, 2856, 1746, 1463, 1361, 1288, 1256, 1206, 1159, 1092, 1050, 836, 776. cis-Isomer: [α]D20 -18.2 (c, 1, CHCl3, 1H NMR (300 MHz, CDCl3, δ, 0.03 (s, 6 H, 2 x Me, 0.88 (s, 9 H, 3 x Me, 1.18-1.25 (m, 2 H, 1.46-1.73 (m, 5 H, 1.79-1.84 (m, 1 H, 2.38 (dd, J, 5.8, 14.7 Hz, 1 H, 2.53 dd, J, 7.5, 14.7 Hz
    • -1.
  • 32
    • 44349115322 scopus 로고    scopus 로고
    • -1.
    • -1.
  • 36
    • 44349172650 scopus 로고    scopus 로고
    • trans-1: [α]D20 -11.3 (c, 0.25, CHCl3, 1H NMR (300 MHz, CDCl3, δ, 1.35-1.39 (m, 2 H, 1.62-1.91 (m, 4 H, 1.90 (dd, J, 1.5, 6.8 Hz, 3 H, 2.44 (dd, J, 5.8, 14.9 Hz, 1 H, 2.62 (dd, J, 6.6, 15.2 Hz, 1 H, 2.66 (dd, J, 8.1, 14.9 Hz, 1 H, 2.88 (dd, J, 6.6, 15.2 Hz, 1 H, 3.66 (s, 3 H, 4.17-4.30 (m, 2 H, 6.13 (dq, J, 1.5, 15.6 Hz, 1 H, 6.85 (dq, J, 6.8, 15.6 Hz, 1 H, 13C NMR (75 MHz, CDCl3, δ, 18.6, 23.5, 31.2, 31.5, 41.9, 47.0, 51.9, 74.8, 75.0, 132.7, 143.6, 172.0, 198.8. IR: 2938, 2860, 1739, 1668, 1626, 1433, 1373, 1352, 1289, 1200, 1066 cm-1. HRMS (CI, m/z [M, H, calcd for C13H21O4: 241.1440; found: 241.1436. Chiral HPLC: ChiralPak AD, hexane-i-PrOH (90:10, λ, 225 nm, flow rate: 0.5 mL/min, tR, 22.4 min m
    • R = 22.4 min (minor) and 25.5 min (major).
  • 37
    • 44349130092 scopus 로고    scopus 로고
    • -1.
    • -1.
  • 38
    • 44349126430 scopus 로고    scopus 로고
    • cis-1: [α]D20 +10.0 (c, 0.94, CHCl3, 1H NMR (300 MHz, CDCl3, δ, 1.12-1.27 (m, 3 H, 1.49-1.66 (m, 3 H, 1.89 (dd, J, 1.5, 6.9 Hz, 3 H, 2.37 (dd, J, 5.6, 14.9 Hz, 1 H, 2.46-2.53 (m, 2 H, 2.80 (dd, J, 6.8, 15.3 Hz, 1 H, 3.65 (s, 3 H, 3.69-3.86 (m, 2 H, 6.13 (dq, J, 1.5, 15.6 Hz, 1 H, 6.84 (dq, J, 6.9, 15.6 Hz, 1 H, 13C NMR (75 MHz, CDCl3, δ, 18.6, 23.5, 31.2, 31.5, 42.9, 47.0, 51.8, 74.8, 75.0, 132.7, 143.6, 172.0, 198.8. IR: 2937, 2857, 1740, 1668, 1627, 1434, 1375, 1350, 1289, 1198, 1066 cm-1. HRMS (CI, m/z [M, H, calcd for C13H21O 4: 241.1440; found: 241.1437. Chiral HPLC: ChiralPak AD, hexane-i-PrOH (90:10, λ, 225 nm, flow rate: 0.5 mL/min, tR, 18.2 min (minor) and 19.9 min major
    • R = 18.2 min (minor) and 19.9 min (major).
  • 39
    • 41049099493 scopus 로고    scopus 로고
    • After submission of this manuscript, a similar approach was reported in the literature, see
    • After submission of this manuscript, a similar approach was reported in the literature, see: Bates, R. W.; Palani, K. Terahedron Lett. 2008, 49, 2832.
    • (2008) Terahedron Lett , vol.49 , pp. 2832
    • Bates, R.W.1    Palani, K.2


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