Stereodivergent Attached-Ring Synthesis via Non-Covalent Interactions: A Short Formal Synthesis of Merrilactone A

Abstract

A strategy to control the diastereoselectivity of bond formation at a prochiral attached-ring bridgehead is reported. An unusual stereodivergent Michael reaction relies on basic vs. Lewis acidic conditions and non-covalent interactions to control re- vs. si- facial selectivity en route to fully substituted attached-rings. This divergency reflects differential engagement of one rotational isomer of the attached-ring system. The successful synthesis of an erythro subtarget diastereomer ultimately leads to a short formal synthesis of merrilactone A.

Publisher

Wiley Verlag

Publication Date

1-17-2022

Publication Title

Angewandte Chemie-International Edition

Department

Chemistry and Biochemistry

Document Type

Article

DOI

https://dx.doi.org/10.1002/anie.202114514

Keywords

Attached ring, Diastereoselectivity, Michael addition, Natural productions, Synthesis design

Language

English

Format

text

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