Phosphate tether-mediated ring-closing metathesis for the generation of P-stereogenic, Z-configured bicyclo[7.3.1]- and bicyclo[8.3.1]phosphates

Jana L. Markley, Soma Maitra, Paul R. Hanson

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

A phosphate tether-mediated ring-closing metathesis (RCM) study to the synthesis of Z-configured, P-stereogenic bicyclo[7.3.1]- and bicyclo[8.3.1]phosphates is reported. Investigations suggest that C3-substitution, olefin substitution, and proximity of the forming olefin to the bridgehead carbon of the bicyclic affect the efficiency and stereochemical outcome of the RCM event. This study demonstrates the utility of phosphate tether-mediated desymmetrization of C2-symmetric, 1,3-anti-diol-containing dienes in the generation of macrocyclic phosphates with potential synthetic and biological utility.

Original languageEnglish (US)
Pages (from-to)899-911
Number of pages13
JournalJournal of Organic Chemistry
Volume81
Issue number3
DOIs
StatePublished - Feb 5 2016
Externally publishedYes

Bibliographical note

Funding Information:
This investigation was generously supported by funds provided by the National Institute of General Medical Sciences (NIH R01 GM077309). The authors thank Justin Douglas and Sarah Neuenswander in the University of Kansas NMR Laboratory and Dr. Todd Williams for HRMS analysis. Support for the NMR instrumentation was provided by NSF Grant nos. 9512331, 9977422, and 0320648 and NIH Center Grant nos. P20 GM103418, S10RR024664, and S10 OD016360. We kindly acknowledge Dr. Victor Day of the Molecular Structure Group (MSG) at the University of Kansas for X-ray analysis (NSF-MRI grant CHE-0923449). The authors thank the University of Kansas and the State of Kansas for support of our program. The authors also thank Materia, Inc. for supplying metathesis catalysts.

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