Total Synthesis of Ciguatoxin CTX3C Masahiro Hirama, Tohru Oishi, Hisatoshi Uehara, Masayuki Inoue, Megumi Maruyama, Hiroki Oguri, and Masayuki Satake

Supplementary Material

Selected physical data for synthetic CTX3C (2): ¹H NMR (600 MHz, C₅D₅N, 25 °C): 0.91 (3H, d, J = 7 Hz, Me54), 0.97 (3H, d, J = 7 Hz, Me57), 1.23-1.32 (9H, m, Me53, 55, 56), 1.49-1.56 (1H, m, H35), 1.60 (1H, dq, J = 10, 7 Hz, H48), 1.63-1.98 (11H, m, H10, 32, 35, 36, 37, 40, 47, 50x2, 51x2), 2.02 (1H, brd, J = 15 Hz, H37), 2.23-2.33 (4H, m, H17, 22, 25, 32), 2.40-2.61 (6H, m, H4, 10, 28x2, 40, 43), 2.67 (1H, ddd, J = 16, 8, 4 Hz, H4), 2.82-2.88 (1H, m, H17), 2.95-3.08 (2H, m, H22, 25), 3.20 (1H, dd, J = 10, 4 Hz, H42), 3.17-3.23 (1H, m, H38), 3.28-3.39 (4H, m, H9, 31, 33, 39), 3.43 (1H, t, J = 9 Hz, H8), 3.43 (1H, t, J = 9 Hz, H11), 3.40-3.50 (2H, m, H5, 34), 3.53 (1H, t, J = 9 Hz, H6), 3.55-3.75 (4H, m, H16, 21, 26, 27), 3.85-3.90 (2H, m, H52x2), 3.94 (1H, t, J = 10 Hz, H46), 4.04 (1H, brd, J = 10 Hz, H45), 4.05-4.20 (6H, m, H1, 7, 12, 15, 20, 29), 4.21 (1H, brs, H44), 4.33 (1H, dd, J = 16, 6 Hz, H1), 4.45-4.50 (1H, m, H41), 5.71-5.77 (1H, m, H3), 5.81-5.89 (3H, m, H2, 13, 18), 5.93 (1H, brd, J = 13 Hz, H14), 5.98 (1H, dd, J = 11, 5 Hz, H19), 6.00-6.06 (2H, m, H23, 24); MALDI-TOF MS calcd for C₅₇H₈₂O₁₆Na [M+Na]⁺ 1045.5501; found 1045.5553; CD (MeOH, 1.0x10^-5 M) _ext 203 nm ( -5), [natural 2 (MeOH, 1.0 x10^-3 M) _ext 203 nm ( -7)].

---

Supplemental Figure 1.

Medium version | Full size version

---

Supplemental Figure 2.

Medium version | Full size version