# A Divergent Asymmetric Total Synthesis of Coprophilin and Four Trichodermic Acids via a [1,5]-Hydride Shift–Aldol Cascade

## TL;DR

The paper describes a new method to synthesize coprophilin and trichodermic acids using a novel cascade reaction and other key chemical steps.

## Contribution

A new [1,5]-hydride shift–aldol cascade reaction is introduced for efficient synthesis of complex natural products.

## Key findings

- An aluminum-promoted [1,5]-hydride shift–aldol cascade was used to build the bicyclic core of the natural products.
- The method allows divergent functionalization of the core structure for multiple target syntheses.
- Key transformations include exo-selective Diels–Alder and Fleming–Tamao oxidation for late-stage modifications.

## Abstract

The asymmetric syntheses
of coprophilin and four members
of the
trichodermic acid family of natural products are disclosed. Our work
employs a number of key transformations, including an aluminum-promoted
[1,5]-hydride shift–aldol cascade reaction, an exo-selective Diels–Alder cycloaddition, and a late-stage Fleming–Tamao
oxidation. These key steps efficiently construct the bicyclic core
of the natural products, which can then be readily functionalized
in a divergent manner, allowing the synthesis of a wide range of natural
product targets.