Synthesis of (±)- andMeso-Limatulone, Defensive Triterpene Metabolites of the LimpetCollisella Limatula

Author:

Mori Kenji,Takikawa Hirosato,Kido Masaru,Albizati K. F.,Faulkner D. John

Publisher

Informa UK Limited

Subject

Molecular Medicine

Reference12 articles.

1. Limatulone, a potent defensive metabolite of the intertidal limpet Collisella limatula

2. Ultrasound-promoted cycloadditions in the synthesis of Salvia miltiorrhiza abietanoid o-quinones

3. Alkaline-Earth Borohydrides and their Applications in Organic Syntheses

4. Synthesis of allylic halides and 1,5-dienes from allylic alcohols

5. Properties of13a: colorless rods fromn-hexane, m.p. 95–97°C; IR (KBr) vmax 3450 (s), 2940 (s), 2860 (s), 1250 (m), 1085 (s), 1065 (s), 1030 (m), 835 (s), 775 (s) cm−1;1H-NMR (300 MHz in CDCl3) δ 0.08 (12H, s) 0.69 (6H, s), 0.91 (18H, s), 1.02 (2H, br d,J= 13 Hz), 1.40–1.70 (4H, m), 1.89 (2H, br d,J= 13 Hz), 2.00–2.25 (6H, m), 2.46 (2H, dt,J= 5, 13 Hz), 3.49 (2H, d,J= 10 Hz), 3.60 (2H, d,J= 10 Hz), 3.86 (2H, s), 4.38 (2H, s), 5.28 (2H, br s);13C-NMR (22.4 MHz in C6D6) δ -5.5, 18.4, 19.3, 23.1, 26.1, 27.6, 28.9, 31.9, 40.1, 71.7, 72.1, 125 4, 139.5. (Found: C, 67.82; H, 11.06. C32H62O4Si2requires: C, 67.79; H, 11.02%)

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