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Synthesis of the termite defensive trinervitanes possessing the unique IN-OUT skeleton

具有独特IN-OUT骨架的白蚁防御性trinervitanes的合成

基本信息

批准号：
09640647
负责人：
KATO Tadahiro
金额：
$ 1.6万
依托单位：
Faculty of Science,Science University of Tokyo
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
1997
资助国家：
日本
起止时间：
1997 至 1999
项目状态：
已结题

项目摘要

Several species of termite soldiers inhabiting in the tropics are known to secrete their defensive substances, from which a varieties of cyclic diterpenes were characterized by G.D.Prestwich and his co-workers. The diterpenes are composed of bicyclics known as 2, 3-dihydroxy secotrinervitane, tricyclics as exemplified by 2, 3-dihydroxytrinervitanes, and tetracyclics as typified by kempan. The plausible biogenesis of these skeletons are suggested to commence from geranylgeranyl-OPP to monocyclic neocembrene, well known as a trail pheromone of the termite workers. The six membered ring formation causes the construction of bicyclic secotrinervitane skeleton, which seems the common intermediate for the further cyclization to the trinervitane and kempane skeletons. Based on the biogenetical route, we have already achieved the synthesis of secotrinervitane type diterpene. By the aids of financial support of Grant-in-Aid for Scientific Research c, we have further continued the effects to explore the synthetic route to the trinervitane and kempane skeletons featuring the biogenesis and succeeded the construction of both skeletons from the secotrinervitane.

已知几种栖息在热带地区的白蚁士兵分泌它们的防御物质，G.D.Prestwich和他的同事从这些物质中鉴定出各种环状二萜。二萜类由称为2，3-二羟基断三脉维生素的双环类、以2，3-二羟基断三脉维生素为例的三环类和以kempan为代表的四环类组成.这些骨骼的合理的生物起源建议开始从香叶基香叶基-β-单环新柏木烯，众所周知的线索信息素的白蚁工人。六元环的形成导致了双环断三脉草烷骨架的构建，这似乎是进一步环化成三脉草烷和kempane骨架的共同中间体。基于生物合成路线，我们已经实现了secotrinervitane型二萜的合成。在科研补助金c的资助下，我们进一步继续探索了具有生物起源特征的trinervitane和kempane骨架的合成路线，并成功地构建了secotrinervitane骨架。

项目成果

期刊论文数量（10）

专著数量（0）

科研奖励数量（0）

会议论文数量（0）

专利数量（0）

加藤忠弘,田中元之,星川雅浩,八木愼: "An Efficient Construction of Trinervitame and Kempone Skeletons from the Common Intermediste" Tetrahedrom Letters. 39. 7553-7556 (1998)

Tadahiro Kato、Motoyuki Tanaka、Masahiro Hoshikawa、Shin Yagi：“从常见的 Intermediste 中高效构建 Trinervitame 和 Kempone 骨架”Tetrahedrom Letters 39。7553-7556 (1998)。