Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, NJ 08854, USA.
Beilstein J Org Chem. 2011;7:937-43. doi: 10.3762/bjoc.7.104. Epub 2011 Jul 5.
The synthesis of a model endocyclic allene related to the vernonia allenes is described. Fragmentation of a suitable decalin derivative gave the simplified germacrane scaffold. Computational analysis of this and related substrates provides insight into the stereoelectronic requirements of C-C fragmentation. The overall strategy to access these and other sesquiterpenes and the key steps in the present sequence are also discussed.
描述了一种与 Vernonia 烯有关的模型内环丙二烯的合成。合适的十氢萘衍生物的碎裂得到了简化的大根香叶烷支架。对这和相关底物的计算分析提供了对 C-C 碎裂的立体电子要求的深入了解。还讨论了获得这些和其他倍半萜的总体策略以及本序列中的关键步骤。
