Hydrochloric Acid → HCID 53739123, compound

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Reaction Steps

The cyclopentanonetriester of formula IV, dimethyl cis,trans-3-(6-carbomethoxy-2-hexenyl)-4-(3-hydroxy-1-octenyl)-2-oxo-1,3-cyclopentanedicarboxylate (11.2 g), described in Example 82, is heated to reflux for 1 hr. in a solution of sodium hydroxide (13.4 g) in 80 ml of water and 110 ml of methanol. The mixture is cooled, adjusted to pH 5 with 2 N HCl, diluted with saturated sodium chloride solution and extracted with ether. The ether extract is dried (Na2SO4) and concentrated to yield the title compound as a mixture of C15 epimers is separated by silica gel chromatography using hexane: chloroform: acetic acid: 10:20:1. The less polar epimer is designated epimer A, nmr (CDCl3) δ 1.05 (t, J=5, 3H), 4.20 (1H), 5.33-5.78 (1H), 6.38 (2H). The more polar epimer is designated epimer B, nmr (CDCl3) δ 1.05 (t, J=5, 3H) 4.18 (1H), 5.30-5.77 (1H), 6.74 (2H).

Provenance & Evidence