Application of Carbohydrate-Templated Asymmetric Diels-Alder Reaction to the Syntheses of ent-Penicillones A and B

作者：Weng Chia Hao; Hsu Day Shin^*; Liao Chun Chen^*

来源：Journal of Organic Chemistry, 2016, 81(22): 11421-11426.

DOI：10.1021/acs.joc.6b02055

Total syntheses of ent-penicillones A (ent-1) and B (ent-2) from 3,5-dimethylcatechol (3) were accomplished in 10 and 9 synthetic steps, respectively. A carbohydrate-templated asymmetric intramolecular Diels- Alder reaction of a masked o-benzoquinone (MOB) 9 and an aqueous acid-catalyzed intramolecular aldol reaction are the key synthetic steps. In addition, the absolute configurations of the bicyclo[2.2.2]oct-5-en-2-one core obtained from the per-Obenzylated alpha-D-glucopyranosyl as a carbohydrate template in the intramolecular Diels Alder reaction of MOBs were revised.

• 出版日期2016-11-18
• 单位清华大学