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A synthesis of (+)-calopin (1a) was achieved employing a highly stereoselective ene reaction between 8-phenylmenthyl glyoxylate (3) and the β,β-dimethylstyrene 4c. Transesterification of the resulting homoallylic alcohol 5c, followed by allylic oxidation and hydrogenation yielded the δ-lactone 13 which was deprotected to the natural product 1a.
(E,E)-Storniamide A nonamethyl ether is obtained from 3-(3,4,5-trimethoxyphenyl)-pyruvic acid and 2-(4-hydroxyphenyl)ethylamine in three steps with an overall yield of 19%.
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