All-carbon [3 + 2] Cycloaddition in Natural Product Synthesis

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2020 Dec 28

PMID 33363670

Citations 5

Authors

Zhuo Wang

Junyang Liu

Affiliations

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Abstract

Many natural products possess interesting medicinal properties that arise from their intriguing chemical structures. The highly-substituted carbocycle is one of the most common structural features in many structurally complicated natural products. However, the construction of highly-substituted, stereo-congested, five-membered carbocycles containing all-carbon quaternary center(s) is, at present, a distinct challenge in modern synthetic chemistry, which can be accessed through the all-carbon [3 + 2] cycloaddition. More importantly, the all-carbon [3 + 2] cycloaddition can forge vicinal all-carbon quaternary centers in a single step and has been demonstrated in the synthesis of complex natural products. In this review, we present the development of all-carbon [3 + 2] cycloadditions and illustrate their application in natural product synthesis reported in the last decade covering 2011-2020 (inclusive).

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