SYNTHESIS, ACTIVITY, AND REACTIVITY OF 9-BORASTEROIDS

建议通过两种截然不同的路线来制备外消旋可的松。 以及使用一种可拆分的起始材料的光学活性可的松 在这些途径中，皮质类固醇的总体方法是对 硼的环化反应(氢化、碳化或等效反应) 作为一种合成工具。此外，雄甾二酮的合成， 无花果、Hibanone、Kaurene与蚜虫的基本骨架系统 (和类似的化合物)被提出使用新开发的变体 关于硼的年化。这些命题是精心设计的(A) 评估合成类固醇(和天然产物)的新方法，(B) 提供医学上重要的药物(可的松等)，以及允许 评价(测试)一类新的“杂化”--类固醇(波罗的亚)和 (C)回答有关使用的某些重要化学问题 复杂天然产物合成中的碳硼烷。这是一种化学物质 三烯将转化为可的松并在光学上 活性可的松。已经设计了各种双烯来评估这种效果 “远程”Lewis碱及其他对氢化/羰化反应的影响 形成其他天然产物的目标体系。所有化合物 准备好的将进行活性评估，一般筛选将在 Lederle‘制药公司，壳牌石油和某些特定类型的活动 (抗癌、抗白血病)在南卡罗来纳州做。

It is proposed to prepare racemic cortisone by two very different routes and optically active cortisone using a resolved starting material for one of these routes the overall approach to the corticoid steroids is a test of boron annelation (hydroboration and carbonylation or equivalent reaction) as a synthetic tool. In addition the synthesis of androstandione, fichtelite, hibanone, kaurene and the basic skeletal system of aphidicolin (and similar compounds) are proposed employing newly developed variations on boron annelation. These propositions are designed (a) to carefully evaluate a new approach to steroid (and natural product) synthesis, (b) to provide medicinally important drugs (cortisone, etc.), as well as allow for evaluation (testing) of a new class of "hetero"-steroids (borasteroids) and (c) to answer certain important chemical questions concerning the usage of carboranes in complex natural product synthesis. It is of chemical significance that a triene will be converted to cortisone and optically active cortisone. Various dienes have been designed to evaluate the effect of "remote" Lewis base and other influences on hydroboration/carbonylation in forming the other natural product target systems. All compounds prepared will be evaluated for actvity with general screening being done at Lederle' Drug Co., Shell Oil and with certain specific types of activity (anticancer, antileukemic) being done at U.S.C.