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The Synthesis of Deoxyfusapyrone. 2. Preparation of the Bis-Trisubstituted Olefin Fragment and Its Attachment to the Pyrone Moiety

“…1 H NMR (400 MHz, CDCl 3 ) δ 3.80 (dd, J = 9.7, 7.0 Hz, 1H), 3.70 (s, 3H), 3.67 (dd, J = 9.7, 6.2 Hz, 1H), 2.70−2.65 (m, 1H), 1.16 (d, J = 7.1 Hz, 3H), 0.90 (s, 3H), 0.06 (s, 6H). All spectral data compare well with the literature data 9b…”

“…1 H NMR (400 MHz, CDCl 3 ) δ 3.67 (dd, J = 9.9, 4.6 Hz, 1H), 3.59−3.50 (m, 3H), 2.99 (s, 1H), 1.92−1.85 (m, 1H), 0.88 (s, 9H), 0.82 (d, J = 6.9 Hz, 3H), 0.04 (s, 6H); 13 C NMR (100.6 MHz, CDCl 3 ) APT δ 68.2 (+), 67.6 (+), 37.2 (−), 25.8 (−), 18.1 (+), 13.1 (−), −5.6 (−). All spectral data compare well with the literature data 9b…”

“…[α] 24 D + 4.44 ( c 4.73, CHCl 3 ); 1 H NMR (400 MHz, CDCl 3 ) δ 7.79 (d, J = 8.0 Hz, 2H), 7.34 (d, J = 8.0 Hz, 2H), 4.03 (dd, J = 9.4, 5.9 Hz, 1H), 3.93 (dd, J = 9.0, 5.6 Hz, 1H), 3.51 (dd, J = 9.9, 4.9 Hz, 1H), 3.42 (dd, J = 9.9, 6.4 Hz, 1H), 2.45 (s, 3H), 1.98−1.94 (m 1H), 0.89 (d, J = 6.9 Hz, 3H), 0.83 (s, 9H), −0.01 (s, 6H); 13 C NMR (100.6 MHz, CDCl 3 ) APT δ 144.6 (+), 133.2 (+), 129.8 (−), 127.9 (−), 72.1 (+), 63.7 (+), 35.7 (−), 25.8 (−), 21.6 (−), 18.1 (+), 13.2 (−), −5.6 (−); IR (neat) 1599, 1252, 1189, 1178, 1098 cm -1 . All spectral data compare well with the literature data 9b…”

The Synthesis of Deoxyfusapyrone. 2. Preparation of the Bis-Trisubstituted Olefin Fragment and Its Attachment to the Pyrone Moiety

“…1 H NMR (400 MHz, CDCl 3 ) δ 3.80 (dd, J = 9.7, 7.0 Hz, 1H), 3.70 (s, 3H), 3.67 (dd, J = 9.7, 6.2 Hz, 1H), 2.70−2.65 (m, 1H), 1.16 (d, J = 7.1 Hz, 3H), 0.90 (s, 3H), 0.06 (s, 6H). All spectral data compare well with the literature data 9b…”

“…1 H NMR (400 MHz, CDCl 3 ) δ 3.67 (dd, J = 9.9, 4.6 Hz, 1H), 3.59−3.50 (m, 3H), 2.99 (s, 1H), 1.92−1.85 (m, 1H), 0.88 (s, 9H), 0.82 (d, J = 6.9 Hz, 3H), 0.04 (s, 6H); 13 C NMR (100.6 MHz, CDCl 3 ) APT δ 68.2 (+), 67.6 (+), 37.2 (−), 25.8 (−), 18.1 (+), 13.1 (−), −5.6 (−). All spectral data compare well with the literature data 9b…”

“…[α] 24 D + 4.44 ( c 4.73, CHCl 3 ); 1 H NMR (400 MHz, CDCl 3 ) δ 7.79 (d, J = 8.0 Hz, 2H), 7.34 (d, J = 8.0 Hz, 2H), 4.03 (dd, J = 9.4, 5.9 Hz, 1H), 3.93 (dd, J = 9.0, 5.6 Hz, 1H), 3.51 (dd, J = 9.9, 4.9 Hz, 1H), 3.42 (dd, J = 9.9, 6.4 Hz, 1H), 2.45 (s, 3H), 1.98−1.94 (m 1H), 0.89 (d, J = 6.9 Hz, 3H), 0.83 (s, 9H), −0.01 (s, 6H); 13 C NMR (100.6 MHz, CDCl 3 ) APT δ 144.6 (+), 133.2 (+), 129.8 (−), 127.9 (−), 72.1 (+), 63.7 (+), 35.7 (−), 25.8 (−), 21.6 (−), 18.1 (+), 13.2 (−), −5.6 (−); IR (neat) 1599, 1252, 1189, 1178, 1098 cm -1 . All spectral data compare well with the literature data 9b…”

Synthesis of All the Stereoisomers of 13,17-Dimethyl-1-tritriacontene and 13,17-Dimethyl-1-pentatriacontene, the Contact Sex Pheromone Components of the Female Tsetse Fly, Glossina austeni

“…[1] They are 13,17-dimethyl-1-tritriacontene (1, Scheme 1) and 13,17-dimethyl-1-pentatriacontene (2), both with two stereogenic centers.…”

Highly Stereocontrolled Total Synthesis of β-d-Mannosyl Phosphomycoketide: A Natural Product from Mycobacterium tuberculosis

“…1 (m, 41H), 1.00−0.80 (m, 18H); 13 C NMR (CDCl 3 ) δ 138.9, 137. 4, 136.8, 128.4, 127.73, 127.71, 127.57, 127.56, 127.51, 127.46, 72.99, 72.97, 70.8, 51.2, 40.2, 37.61, 37.58, 37.55, 37.53, 37.51, 37.4, 37.3, 37.2, 37.12, 37.08, 36.9, 34.9, 34.1, 33.7, 33.6, 33.4, 32.96, 32.95, 32.94, 32.91, 32.90, 32.1, 31.7, 30.2, 29.6, 28.4, 27.9, 27.8 (27). CuSO 4 (62 mg, 0.39 mmol) was added to a solution of 8-benzoxy-1-(tert-butyldiphenylsilyloxy)-(2R,6R)-2,6-dimethyl-(Z/E)-4-octene (15) (1.96 g, 3.91 mmol) and hydrazine (12.3 mL, 391 mmol) in ethanol (200 mL).…”

The Synthesis of Deoxyfusapyrone. 2. Preparation of the Bis-Trisubstituted Olefin Fragment and Its Attachment to the Pyrone Moiety

“…1 H NMR (400 MHz, CDCl 3 ) δ 3.80 (dd, J = 9.7, 7.0 Hz, 1H), 3.70 (s, 3H), 3.67 (dd, J = 9.7, 6.2 Hz, 1H), 2.70−2.65 (m, 1H), 1.16 (d, J = 7.1 Hz, 3H), 0.90 (s, 3H), 0.06 (s, 6H). All spectral data compare well with the literature data 9b…”

“…1 H NMR (400 MHz, CDCl 3 ) δ 3.67 (dd, J = 9.9, 4.6 Hz, 1H), 3.59−3.50 (m, 3H), 2.99 (s, 1H), 1.92−1.85 (m, 1H), 0.88 (s, 9H), 0.82 (d, J = 6.9 Hz, 3H), 0.04 (s, 6H); 13 C NMR (100.6 MHz, CDCl 3 ) APT δ 68.2 (+), 67.6 (+), 37.2 (−), 25.8 (−), 18.1 (+), 13.1 (−), −5.6 (−). All spectral data compare well with the literature data 9b…”

“…[α] 24 D + 4.44 ( c 4.73, CHCl 3 ); 1 H NMR (400 MHz, CDCl 3 ) δ 7.79 (d, J = 8.0 Hz, 2H), 7.34 (d, J = 8.0 Hz, 2H), 4.03 (dd, J = 9.4, 5.9 Hz, 1H), 3.93 (dd, J = 9.0, 5.6 Hz, 1H), 3.51 (dd, J = 9.9, 4.9 Hz, 1H), 3.42 (dd, J = 9.9, 6.4 Hz, 1H), 2.45 (s, 3H), 1.98−1.94 (m 1H), 0.89 (d, J = 6.9 Hz, 3H), 0.83 (s, 9H), −0.01 (s, 6H); 13 C NMR (100.6 MHz, CDCl 3 ) APT δ 144.6 (+), 133.2 (+), 129.8 (−), 127.9 (−), 72.1 (+), 63.7 (+), 35.7 (−), 25.8 (−), 21.6 (−), 18.1 (+), 13.2 (−), −5.6 (−); IR (neat) 1599, 1252, 1189, 1178, 1098 cm -1 . All spectral data compare well with the literature data 9b…”

Synthesis of All the Stereoisomers of 13,17-Dimethyl-1-tritriacontene and 13,17-Dimethyl-1-pentatriacontene, the Contact Sex Pheromone Components of the Female Tsetse Fly, Glossina austeni

“…[1] They are 13,17-dimethyl-1-tritriacontene (1, Scheme 1) and 13,17-dimethyl-1-pentatriacontene (2), both with two stereogenic centers.…”

Highly Stereocontrolled Total Synthesis of β-d-Mannosyl Phosphomycoketide: A Natural Product from Mycobacterium tuberculosis

“…1 (m, 41H), 1.00−0.80 (m, 18H); 13 C NMR (CDCl 3 ) δ 138.9, 137. 4, 136.8, 128.4, 127.73, 127.71, 127.57, 127.56, 127.51, 127.46, 72.99, 72.97, 70.8, 51.2, 40.2, 37.61, 37.58, 37.55, 37.53, 37.51, 37.4, 37.3, 37.2, 37.12, 37.08, 36.9, 34.9, 34.1, 33.7, 33.6, 33.4, 32.96, 32.95, 32.94, 32.91, 32.90, 32.1, 31.7, 30.2, 29.6, 28.4, 27.9, 27.8 (27). CuSO 4 (62 mg, 0.39 mmol) was added to a solution of 8-benzoxy-1-(tert-butyldiphenylsilyloxy)-(2R,6R)-2,6-dimethyl-(Z/E)-4-octene (15) (1.96 g, 3.91 mmol) and hydrazine (12.3 mL, 391 mmol) in ethanol (200 mL).…”

The Synthesis of Deoxyfusapyrone. 2. Preparation of the Bis-Trisubstituted Olefin Fragment and Its Attachment to the Pyrone Moiety

“…1 H NMR (400 MHz, CDCl 3 ) δ 3.80 (dd, J = 9.7, 7.0 Hz, 1H), 3.70 (s, 3H), 3.67 (dd, J = 9.7, 6.2 Hz, 1H), 2.70−2.65 (m, 1H), 1.16 (d, J = 7.1 Hz, 3H), 0.90 (s, 3H), 0.06 (s, 6H). All spectral data compare well with the literature data 9b…”

“…1 H NMR (400 MHz, CDCl 3 ) δ 3.67 (dd, J = 9.9, 4.6 Hz, 1H), 3.59−3.50 (m, 3H), 2.99 (s, 1H), 1.92−1.85 (m, 1H), 0.88 (s, 9H), 0.82 (d, J = 6.9 Hz, 3H), 0.04 (s, 6H); 13 C NMR (100.6 MHz, CDCl 3 ) APT δ 68.2 (+), 67.6 (+), 37.2 (−), 25.8 (−), 18.1 (+), 13.1 (−), −5.6 (−). All spectral data compare well with the literature data 9b…”

“…[α] 24 D + 4.44 ( c 4.73, CHCl 3 ); 1 H NMR (400 MHz, CDCl 3 ) δ 7.79 (d, J = 8.0 Hz, 2H), 7.34 (d, J = 8.0 Hz, 2H), 4.03 (dd, J = 9.4, 5.9 Hz, 1H), 3.93 (dd, J = 9.0, 5.6 Hz, 1H), 3.51 (dd, J = 9.9, 4.9 Hz, 1H), 3.42 (dd, J = 9.9, 6.4 Hz, 1H), 2.45 (s, 3H), 1.98−1.94 (m 1H), 0.89 (d, J = 6.9 Hz, 3H), 0.83 (s, 9H), −0.01 (s, 6H); 13 C NMR (100.6 MHz, CDCl 3 ) APT δ 144.6 (+), 133.2 (+), 129.8 (−), 127.9 (−), 72.1 (+), 63.7 (+), 35.7 (−), 25.8 (−), 21.6 (−), 18.1 (+), 13.2 (−), −5.6 (−); IR (neat) 1599, 1252, 1189, 1178, 1098 cm -1 . All spectral data compare well with the literature data 9b…”

Synthesis of All the Stereoisomers of 13,17-Dimethyl-1-tritriacontene and 13,17-Dimethyl-1-pentatriacontene, the Contact Sex Pheromone Components of the Female Tsetse Fly, Glossina austeni

“…[1] They are 13,17-dimethyl-1-tritriacontene (1, Scheme 1) and 13,17-dimethyl-1-pentatriacontene (2), both with two stereogenic centers.…”

Highly Stereocontrolled Total Synthesis of β-d-Mannosyl Phosphomycoketide: A Natural Product from Mycobacterium tuberculosis

“…1 (m, 41H), 1.00−0.80 (m, 18H); 13 C NMR (CDCl 3 ) δ 138.9, 137. 4, 136.8, 128.4, 127.73, 127.71, 127.57, 127.56, 127.51, 127.46, 72.99, 72.97, 70.8, 51.2, 40.2, 37.61, 37.58, 37.55, 37.53, 37.51, 37.4, 37.3, 37.2, 37.12, 37.08, 36.9, 34.9, 34.1, 33.7, 33.6, 33.4, 32.96, 32.95, 32.94, 32.91, 32.90, 32.1, 31.7, 30.2, 29.6, 28.4, 27.9, 27.8 (27). CuSO 4 (62 mg, 0.39 mmol) was added to a solution of 8-benzoxy-1-(tert-butyldiphenylsilyloxy)-(2R,6R)-2,6-dimethyl-(Z/E)-4-octene (15) (1.96 g, 3.91 mmol) and hydrazine (12.3 mL, 391 mmol) in ethanol (200 mL).…”