（+）-adjunctins C和D的全合成：其绝对构型的确定

Total syntheses of (+)-adunctins C and D: assignment of their absolute configurations.

作者信息

Xiao Jian, Zhao Jun, Wang Ya-Wen, Luo Gan, Peng Yu

机构信息

Sichuan Engineering Research Center for Biomimetic Synthesis of Natural Drugs, School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031, People's Republic of China.

West China School of Pharmacy, Sichuan University, Chengdu 610041, People's Republic of China.

出版信息

Org Biomol Chem. 2021 Nov 25;19(45):9840-9843. doi: 10.1039/d1ob02055b.

DOI:10.1039/d1ob02055b

PMID:34748620

Abstract

The first total synthesis of (+)-adunctin C (-1) and (+)-adunctin D (2), two monoterpene-substitued dihydrochalcones isolated from (Piperaceae), was achieved. A regioselective oxidative [3 + 2] cycloaddition of acylphloroglucinol with (-)-β-phellandrene was developed to construct their unique spirobenzofuran skeleton. The absolute configurations of natural adunctins 1 and 2 were thus assigned through these endeavors.

摘要

实现了从胡椒科植物中分离得到的两种单萜取代二氢查耳酮（+）-adjunctin C（-1）和（+）-adjunctin D（2）的首次全合成。开发了酰基间苯三酚与（-）-β-水芹烯的区域选择性氧化[3 + 2]环加成反应，以构建它们独特的螺苯并呋喃骨架。通过这些努力确定了天然adjunctins 1和2的绝对构型。