Department of Chemical Engineering, Escuela Politécnica Superior, University of Sevilla, 41011 Sevilla, Spain.
Organic Chemistry, ceiA3, CIAIMBITAL, University of Almería, 04120 Almería, Spain.
Mar Drugs. 2023 May 26;21(6):322. doi: 10.3390/md21060322.
Puupehenone and puupehedione are natural products isolated from marine organisms. These compounds display a broad spectrum of biological activities, the in vitro antitubercular activity of puupehenone being a stand out, and are equipped with an interesting structural complexity. These products have served to stimulate the continual interest of the synthetic community. The first part of this article is a review of their total synthesis, using natural compounds which have the potential to be transformed into these marine compounds as starting materials; the synthetic routes employed to generate the basic skeleton; and the advances made to synthesize the pyran C ring with the required diastereoselectivity to obtain the natural products. Finally, this perspective shows a personal reflection of the authors on a possible unified and efficient retrosynthetic route that could allow easy access to these natural products, as well as their epimers at the C8 carbon and which could be used to address future biological issues in the production of pharmacologically active compounds.
普乌酚酮和普乌酚二酮是从海洋生物中分离得到的天然产物。这些化合物具有广泛的生物活性,普乌酚酮的体外抗结核活性尤为突出,并且具有有趣的结构复杂性。这些产物激发了合成界的持续兴趣。本文的第一部分是对它们的全合成的综述,使用具有转化为这些海洋化合物潜力的天然化合物作为起始原料;用于生成基本骨架的合成路线;以及为了获得天然产物而以所需的非对映选择性合成吡喃 C 环所取得的进展。最后,这一观点展示了作者对一种可能的统一和有效的逆合成路线的个人反思,该路线可以方便地获得这些天然产物及其 C8 碳的差向异构体,并且可以用于解决在产生具有药理活性的化合物时的未来生物学问题。