Total syntheses of ML-236A and compactin by combining the lactonic (silyl) enolate rearrangement and aldehyde-diene cyclocondensation technologies

SJ Danishefsky, B Simoneau

Index: Danishefsky, Samuel J.; Simoneau, Bruno Journal of the American Chemical Society, 1989 , vol. 111, # 7 p. 2599 - 2604

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Citation Number: 92

Abstract

0.2 g of K,C03 for 2.5 h. The mixture was filtered, evaporated, taken up in CH2CI2, and washed successively with HzO and brine. Chroma- tography (EtOAc/i-PrOH 98.5:1.5) gave 0.022 g of starting material 6 and 0.468 g of alcohol 7a. The analytical sample was distilled bulb-to- bulb [oven at 145 OC (0.025 mmHg)]: Anal. for C16H29N02: c , H; [a]D = -1 13.1' (c = 0.55, CHCI,); 'H NMR 6 5.28 (br s, 1 H), 3.64 (m, 2 H), 3.00 (s, 3 H), 2.95 (s, 3 H), 2.68 (m, 1 H), ...