Efficient synthetic method for biologically active compounds and their synthetic intermediates by new carbon-carbon bond formation reactions.

该项目涉及研究前列腺素和前列腺素的合成中间体的短而有效的合成，这两种物质都已知具有与包括癌症在内的老年人疾病相关的重要生物活性。2-（苯基硒）-2-环戊烯（或环己烯）-1- 1用三丁基锡锂处理得到烯酸酯，然后用碘化烯丙基捕获得到烯丙烯酮。去癸烯基硒化可以通过许多试剂，如四丁基氟化铵、碱、路易斯酸，或通过热和光处理，产生高产的2-烯丙基-2-环焦炭-1- 1。根据该方案，可由手性的4-硅氧基-2-环戊烯-1- 1直接高收率制备前列腺素及其类似物的关键中间体。该方法包括已知的最短和最方便的过程。在上述过程中，苯硫基和三烷基硅基分别可以取代苯硒基和三烷基锡基。2-（苯基硒）-2-环戊烯-1- 1、三丁基锡锂和醛的三组分偶联制备了2-（1-羟基烷基）-2-环戊烯-1- 1的高收率，为高效合成punaglandins及其类似物开辟了道路。

This project deals with the study on the short and efficient synthesis of the synthetic intermediates of prostaglandins and punaglandins, both of which are known to have important biological activities related to the deseases of old people including cancer.Treatment of 2-(phenylseleno)-2-cyclopenten(or cyclohexen)-1-one with tributylstannyllithium gave the enolate witch was then trapped with allyl iodide to afford the allylated cycloalkenone. Destannylselenenylation could be effected by numerous reagents such as tetrabutylammonium fluoride, bases, Lewis acids, or by thermal and photo treatments, giving 2-allyl-2-cylcoalken-1-one in high yields. According to this protocol, the key intermediate for prostaglandins and their analogs could be prepared in high yield directly from chiral 4-siloxy-2-cyclopenten-1-one. The method comprises the shortest and the most convenient process ever known. In the above procedure the phenylthio and trialkylsilyl groups were shown to be able to be substituted for the phenylseleno and the tributylstannyl groups, respectively.The three-component coupling of 2-(phenylseleno)-2-cyclopenten-1-one, tributylstannyllithium, and aldehydes led to a high yield preparation of 2-(1-hydroxyalkyl)-2-cyclopenten-1-ones, which opened a way to the efficient synthesis of punaglandins and their analogs.