Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science and Peking-Tsinghua Center for Life Sciences, College of Chemistry of Peking University, 202 Chengfu Road, Beijing 100871, China.
Chem Asian J. 2012 Oct;7(10):2321-33. doi: 10.1002/asia.201200363. Epub 2012 Jul 3.
First-generation synthetic strategies for the diastereoselective total synthesis of schindilactone A (1) are presented and methods for the synthesis of the ABC, FGH, and CDEF moieties are explored. We have established a method for the synthesis of the ABC moiety, which included both a Diels-Alder reaction and a ring-closing metathesis as the key steps. We have also developed a method for the synthesis of the FGH moiety, which involved the use of a Pauson-Khand reaction and a carbonylative annulation reaction as the key steps. Furthermore, we have achieved the construction of the central 7-8 bicyclic ring system by using a [3,3]-rearrangement as the key step. However, unfortunately, when this rearrangement reaction was applied to the construction of the more advanced CDEF moiety, the anticipated annulation reaction did not occur and the development of an alternative synthetic strategy would be required for the construction of this central core.
呈现了用于外消旋全合成 schindilactone A（1）的第一代合成策略，并探索了合成 ABC、FGH 和 CDEF 部分的方法。我们已经建立了一种合成 ABC 部分的方法，其中包括 Diels-Alder 反应和环 closing metathesis 作为关键步骤。我们还开发了一种合成 FGH 部分的方法，其中涉及使用 Pauson-Khand 反应和羰基化环加成反应作为关键步骤。此外，我们通过使用[3,3]-重排作为关键步骤实现了中央 7-8 元双环系统的构建。然而，不幸的是，当将该重排反应应用于更先进的 CDEF 部分的构建时，预期的环加成反应并未发生，需要开发替代的合成策略来构建这个中央核心。
