Many terpenoids are biosynthesized after a cascade of cyclizations and rearrangements of carbocations mediated by terpenoid synthases, as exemplified in the biosynthesis of lanosterol. Although several reports of organisms or purified enzymes catalyzing this cascade of reactions in the laboratory have been described, the development of chemical transformations capable of mimicking such tandem cyclizations and rearrangements constitute a formidable challenge for organic chemists. From the very early works of Van Tamelen in the 1960s to our time, we present the Lewis or Brønsted acids-mediated cyclization–rearrangements of carbocations cascades aimed to mimic the action of enzymes. From all the achievements herein presented, the hypothesis of minimal enzymatic participation is reinforced, and this, if confirmed, promises new achievements in this area in the next future.

在萜类化合物合酶介导的碳环化反应的一系列环化和重排后，生物合成了许多类萜，如羊毛甾醇的生物合成中所示。尽管已经描述了在实验室中催化这种级联反应的生物或纯化酶的几种报道，但是能够模仿此类串联环化和重排的化学转化的发展对有机化学家构成了巨大的挑战。从范塔米尔（Van Tamelen）的早期作品到1960年代，我们一直在研究路易斯或布朗斯台德酸介导的环化反应-碳负离子级联反应的重排，旨在模拟酶的作用。从本文介绍的所有成就中，最小化酶参与的假设得到了加强，并且如果得到证实，