Total Synthesis of Illisimonin A and Merrilactone A

Author:

Gong Xu1,Huang Juan1,Sun Xiangrui1,Chen Ziling1,Yang Ming1ORCID

Affiliation:

1. State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering Lanzhou University 222 South Tianshui Road Lanzhou Gansu Province 730000 China

Abstract

AbstractIllicium sesquiterpenes are a large family of biologically active secondary metabolites isolated from Illicium species of plants and are well‐known for their activity of neurite outgrowth in cultured neurons. Herein, we propose a comprehensive biosynthetic pathway for illicium sesquiterpenes and report a synthetic route to illisimonin A and merrilactone A based on it. We think that the carbon scaffolds of most of the illicium sesquiterpenes could be synthesized from a dicarbonyl derivative of allo‐cedrane through retro‐Dieckmann condensation, oxidative cleavage and aldol reaction at suitable oxidation states in Nature. The common intermediate for illisimonin A and merrilactone A similar to the dicarbonyl derivative of allo‐cedrane was assembled with up to 82 % ee by an asymmetric intramolecular desymmetrizing reductive Heck reaction by the use of a new type of chiral phosphine ligand. The syntheses of illisimonin A and merrilactone A supported the key transformations of the proposed biosynthetic pathway.

Funder

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Chemistry,Catalysis

Reference48 articles.

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