Formal Total Synthesis of Atropurpuran.

The Journal of Organic Chemistry
Takahiro SuzukiKeiji Tanino

Abstract

Atropurpuran, isolated from the roots of Aconitum hemsleyanum, is a non-alkaloidal diterpene which possesses a unique pentacyclic skeleton that contains an unprecedented tetracyclo[5.3.3.04,9.04,12]tridecane unit. We report herein the formal total synthesis of atropurpuran. The key features of our synthetic route are a high diastereoselective construction of the tri- and tetrasubstituted carbons (i.e., C4, C5, C10, and C20) through an Yb-catalyzed Mukaiyama aldol reaction in an aqueous medium and a one-pot operation including an intramolecular Diels-Alder reaction/ring-closing metathesis to construct the unique pentacyclic skeleton of atropurpuran.

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Citations

Sep 10, 2020·Angewandte Chemie·Hong-Xiu HuangYong Qin
Dec 23, 2020·Accounts of Chemical Research·Xiao-Yu LiuYong Qin

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