Wharton-fragmentation-based approach to the carbocyclic core of the phomoidrides

Graham K. Murphy; Naoto Hama; Aaron Bedermann; Ping Dong; Chris M. Schneider; Travis C. McMahon; Ran N. Tao; Barry M. Twenter; David A. Spiegel; John L. Wood

doi:10.1021/ol302011b

Wharton-fragmentation-based approach to the carbocyclic core of the phomoidrides

Graham K. Murphy, Naoto Hama, Aaron Bedermann, Ping Dong, Chris M. Schneider, Travis C. McMahon, Ran N. Tao, Barry M. Twenter, David A. Spiegel, John L. Wood

PHA - Molecular Pharmaceutical Science

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

6 Citations (Scopus)

Abstract

The carbocyclic core of the phomoidrides has been synthesized efficiently and in high yield. Key steps include a phenolic oxidation/intramolecular Diels-Alder sequence, tandem radical cyclization, and a late-stage Wharton fragmentation of a densely functionalized isotwistane skeleton.

Original language	English
Pages (from-to)	4544-4547
Number of pages	4
Journal	Organic letters
Volume	14
Issue number	17
DOIs	https://doi.org/10.1021/ol302011b
Publication status	Published - 2012 Sep 7

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol302011b

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Wharton-fragmentation-based approach to the carbocyclic core of the phomoidrides. / Murphy, Graham K.; Hama, Naoto; Bedermann, Aaron; Dong, Ping; Schneider, Chris M.; McMahon, Travis C.; Tao, Ran N.; Twenter, Barry M.; Spiegel, David A.; Wood, John L.

In: Organic letters, Vol. 14, No. 17, 07.09.2012, p. 4544-4547.

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

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author = "Murphy, {Graham K.} and Naoto Hama and Aaron Bedermann and Ping Dong and Schneider, {Chris M.} and McMahon, {Travis C.} and Tao, {Ran N.} and Twenter, {Barry M.} and Spiegel, {David A.} and Wood, {John L.}",

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AU - McMahon, Travis C.

AU - Tao, Ran N.

AU - Twenter, Barry M.

AU - Spiegel, David A.

AU - Wood, John L.

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AB - The carbocyclic core of the phomoidrides has been synthesized efficiently and in high yield. Key steps include a phenolic oxidation/intramolecular Diels-Alder sequence, tandem radical cyclization, and a late-stage Wharton fragmentation of a densely functionalized isotwistane skeleton.

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Wharton-fragmentation-based approach to the carbocyclic core of the phomoidrides

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