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Synthesis 2023; 55(13): 1949-1960
DOI: 10.1055/a-1702-5062
DOI: 10.1055/a-1702-5062
short review
Recognition of Symmetry as a Powerful Tool in Natural Product Synthesis
We thank the National Science Foundation (CHE-1654223) and the NIH/National Institute of General Medical Sciences (R01-GM118644) for financial support. C.S.S. thanks the David and Lucile Packard Foundation, the Alfred P. Sloan Foundation, and the Camille and Henry Dreyfus Foundation.
Abstract
The design of concise and efficient synthetic strategies to access naturally occurring, pharmaceutically active complex molecules is of utmost importance in current chemistry. It not only enables rapid access to these molecules and their analogues but also provides sufficient quantities for their biological evaluation. Identification of any symmetric or pseudosymmetric synthetic intermediates upon retrosynthetic bond disconnection of the target molecule holds the promise to significantly streamline the route towards the compound of interest. This review will highlight recent examples of successful natural product syntheses reported within the past five years that benefited from the recognition of symmetry elements during the retrosynthetic design.
1 Introduction
2 Examples
2.1 Chondrosterin I and J
2.2 (–)-Bilobalide A
2.3 Delavatine A
2.4 Oxycodone
2.5 (–)-20-epi-vincamine and (–)-20-epi-eburnamonine
2.6 Reserpine
2.7 (–)-Berkeleyone A
2.8 (–)-Maximiscin
2.9 Aplysiasecosterol A
2.10 (–)-Batrachotoxinin A
2.11 (–)-Mitrephorone A
3 Conclusions
Publication History
Received: 11 August 2021
Accepted after revision: 22 November 2021
Accepted Manuscript online:
22 November 2021
Article published online:
08 March 2023
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For pioneering efforts, see:
For selected biosynthetic studies see: