NDLI: Ring-Closing Metathesis Approaches towards the Total Synthesis of Rhizoxins

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Ring-Closing Metathesis Approaches towards the Total Synthesis of Rhizoxins

Content Provider	MDPI
Author	Liniger, Marc Neuhaus, Christian Altmann, Karl-Heinz
Copyright Year	2020
Description	Efforts are described towards the total synthesis of the bacterial macrolide rhizoxin F, which is a potent tubulin assembly and cancer cell growth inhibitor. A significant amount of work was expanded on the construction of the rhizoxin core macrocycle by ring-closing olefin metathesis (RCM) between C(9) and C(10), either directly or by using relay substrates, but in no case was ring-closure achieved. Macrocycle formation was possible by ring-closing alkyne metathesis (RCAM) at the C(9)/C(10) site. The requisite diyne was obtained from advanced intermediates that had been prepared as part of the synthesis of the RCM substrates. While the direct conversion of the triple bond formed in the ring-closing step into the C(9)-C(10) E double bond of the rhizoxin macrocycle proved to be elusive, the corresponding Z isomer was accessible with high selectivity by reductive decomplexation of the biscobalt hexacarbonyl complex of the triple bond with ethylpiperidinium hypophosphite. Radical-induced double bond isomerization, full elaboration of the C(15) side chain, and directed epoxidation of the C(11)-C(12) double bond completed the total synthesis of rhizoxin F.
Starting Page	4527
e-ISSN	14203049
DOI	10.3390/molecules25194527
Journal	Molecules
Issue Number	19
Volume Number	25
Language	English
Publisher	MDPI
Publisher Date	2020-10-02
Access Restriction	Open
Subject Keyword	Molecules Organic Chemistry Macrocyclization Macrolactone Natural Products Paterson Aldol Reaction Reductive Decomplexation Rhizoxin Ring-closing Alkyne Metathesis Radical-induced Double Bond Isomerization Ring-closing Olefin Metathesis Total Synthesis
Content Type	Text
Resource Type	Article

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