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Synthesis 2022; 54(14): 3209-3214
DOI: 10.1055/s-0040-1719910
DOI: 10.1055/s-0040-1719910
paper
Stereocontrolled Synthesis of (±)-Grandisol
Financial support from Research Corporation (Cottrell Grant), American Chemical Society Petroleum Research Fund, National Science Foundation (Research with Minority Students Program), National Science Foundation CoAMP and Howard Hughes Medical Institute Biological Sciences Education Initiative is gratefully acknowledged.
Abstract
A synthetic approach to grandisol is described. The route to the cyclobutane core relies on an efficient intramolecular [2+2] cycloaddition that establishes the required cis-ring fusion at the adjacent side chains of the cyclobutane ring. Using a new two-step lithium/halide homologation procedure, norgrandisol was efficiently converted into grandisol. This new approach enables the synthesis of grandisol in five steps from commercially available starting material in 22% overall yield.
Key words
boll weevil - cyclobutene ring - [2+2] cycloaddition - grandisol - photocyclization - homologationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1719910.
- Supporting Information
Publication History
Received: 19 January 2022
Accepted after revision: 10 February 2022
Article published online:
06 April 2022
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