Phosphate tether-mediated ring-closing metathesis for the generation of medium to large, P-stereogenic bicyclo[n.3.1]phosphates

Soma Maitra; Jana L. Markley; Rambabu Chegondi; Paul R. Hanson

doi:10.1016/j.tet.2015.06.016

Phosphate tether-mediated ring-closing metathesis for the generation of medium to large, P-stereogenic bicyclo[n.3.1]phosphates

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

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

Abstract A phosphate tether-mediated ring-closing metathesis study towards the synthesis of P-stereogenic bicyclo[6.3.1]-, bicyclo[7.3.1]-, and bicyclo[8.3.1]phosphates is reported. This study demonstrates expanded utility of phosphate tether-mediated desymmetrization of C₂-symmetric, 1,3-anti-diol dienes in generating complex medium to large, P-stereogenic bicyclo[n.3.1]phosphates.

Original language	English (US)
Article number	26851
Pages (from-to)	5734-5740
Number of pages	7
Journal	Tetrahedron
Volume	71
Issue number	35
DOIs	https://doi.org/10.1016/j.tet.2015.06.016
State	Published - Jul 25 2015
Externally published	Yes

Bibliographical note

Funding Information:
This investigation was generously supported by funds provided by the National Institute of General Medical Sciences ( NIH R01 GM077309-7 ). 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 # 9512331 , # 9977422 , # 0320648 and NIH Center Grant # 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 catalyst.

Publisher Copyright:
© 2015 Elsevier Ltd.

Keywords

Bicyclic phosphate triester
Desymmetrization
P-stereogenic phosphate
Phosphate tether
Ring-closing metathesis
Tripodal coupling

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abstract = "Abstract A phosphate tether-mediated ring-closing metathesis study towards the synthesis of P-stereogenic bicyclo[6.3.1]-, bicyclo[7.3.1]-, and bicyclo[8.3.1]phosphates is reported. This study demonstrates expanded utility of phosphate tether-mediated desymmetrization of C2-symmetric, 1,3-anti-diol dienes in generating complex medium to large, P-stereogenic bicyclo[n.3.1]phosphates.",

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note = "Funding Information: This investigation was generously supported by funds provided by the National Institute of General Medical Sciences ( NIH R01 GM077309-7 ). 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 # 9512331 , # 9977422 , # 0320648 and NIH Center Grant # 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 catalyst. Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd.",

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AU - Markley, Jana L.

AU - Chegondi, Rambabu

AU - Hanson, Paul R.

N1 - Funding Information: This investigation was generously supported by funds provided by the National Institute of General Medical Sciences ( NIH R01 GM077309-7 ). 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 # 9512331 , # 9977422 , # 0320648 and NIH Center Grant # 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 catalyst. Publisher Copyright: © 2015 Elsevier Ltd.

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N2 - Abstract A phosphate tether-mediated ring-closing metathesis study towards the synthesis of P-stereogenic bicyclo[6.3.1]-, bicyclo[7.3.1]-, and bicyclo[8.3.1]phosphates is reported. This study demonstrates expanded utility of phosphate tether-mediated desymmetrization of C2-symmetric, 1,3-anti-diol dienes in generating complex medium to large, P-stereogenic bicyclo[n.3.1]phosphates.

AB - Abstract A phosphate tether-mediated ring-closing metathesis study towards the synthesis of P-stereogenic bicyclo[6.3.1]-, bicyclo[7.3.1]-, and bicyclo[8.3.1]phosphates is reported. This study demonstrates expanded utility of phosphate tether-mediated desymmetrization of C2-symmetric, 1,3-anti-diol dienes in generating complex medium to large, P-stereogenic bicyclo[n.3.1]phosphates.

KW - Bicyclic phosphate triester

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KW - Ring-closing metathesis

KW - Tripodal coupling

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Phosphate tether-mediated ring-closing metathesis for the generation of medium to large, P-stereogenic bicyclo[n.3.1]phosphates

Abstract

Bibliographical note

Keywords

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