Total synthesis of sollasin a and sollasin d via photocycloaddition of methyl 2,4-dioxopentanoate to methyl E-2-methyl-2-butenoate

Chemistry Letters

Volumn , Issue 2, 1998, Pages 113-114

  Hatsui, Toshihide ^a   Taga, Masashi ^a   Mori, Akira ^a   Takeshita, Hitoshi ^b  

^a KYUSHU UNIVERSITY   (Japan)

^b TOHWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032372768     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.113     Document Type: Article

References (23)

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14. Frequently observed ene reaction of 1 with olefins showed the same selectivity.
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23. 13C NMR chemical shifts from the figures cited in ref. 12 are shown in brackets. 18: δ(H)=0.86(3H, d, J=7.0 Hz), 0.87(3H, s), 1.46(2H, m), 1.52(2H, m), 1.60(3H, td, J=2.3, 1.1 Hz), 1.67(1H, m), 1.68(1H, m), 1.79(1H, m), 1.95(2H, m), 2.07(1H, m), 2.17(3H, d, J=1.1 Hz), 3.68(3H, s), 5.44(1H, br s), and 5.66(1H, qm, J=1.1 Hz); δ(C)=15.8(+0.1), 19.1(2C, ±0), 21.0(±0), 25.5(±0), 26.9(±0), 33.3(±0), 34.4(±0), 35.7 (±0), 40.4(-0.1), 50.8(±0), 114.6(±0), 124.7(±0), 139.0 (±0), 161.6(±0), and 167.3(±0). 20: δ(H)=0.88(3H, d, J=6.0 Hz), 0.89(3H, s), 1.45(2H, m), 1.54(2H, m), 1.61(3H, td, J=2.3, 1.1 Hz), 1.70(1H, m), 1.81(1H, m), 1.95(2H, m), 2.09(1H, m), 2.12(3H, brs), 3.80(3H, s), 5.41(1H, d, J=2.2 Hz), 5.45(1H, brs), 5.77(1H, brs), and 5.78(1H, d, J=2.2 Hz); δ(C)=15.8 (±0), 19.1(±0), 19.6(±0), 21.0(±+0), 27.0(+0.1), 25.5 (±0), 33.3 (±0), 34.7(±0), 36.5(±0), 40.5(±0), 55.7(±0), 87.4 (±0), 100.7(±0), 116.3(±0), 124.6(-0.1), 139.0(±0), 151.3(-0.1), 160.4(±0), 164.5(±0), and 171.4(±0).