Toward the synthesis of phomoidride D

Graham K. Murphy; Tatsuya Shirahata; Naoto Hama; Aaron Bedermann; Ping Dong; Travis C. McMahon; Barry M. Twenter; David A. Spiegel; Ivar M. McDonald; Nobuaki Taniguchi; Munenori Inoue; John L. Wood

doi:10.1021/jo302353g

Toward the synthesis of phomoidride D

Graham K. Murphy, Tatsuya Shirahata, Naoto Hama, Aaron Bedermann, Ping Dong, Travis C. McMahon, Barry M. Twenter, David A. Spiegel, Ivar M. McDonald, Nobuaki Taniguchi, Munenori Inoue, John L. Wood

PHA - Molecular Pharmaceutical Science

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

14 Citations (Scopus)

Abstract

An efficient and highly stereoselective approach toward the phomoidride family of natural products is described. The carbocyclic core structure was assembled using a tandem phenolic oxidation/Diels-Alder cycloaddition and a tandem 5-exo-trig/5-exo-trig radical cyclization to deliver an isotwistane intermediate that, upon a late-stage xanthate-initiated Grob fragmentation, furnishes the requisite bicyclo[4.3.1]decene.

Original language	English
Pages (from-to)	477-489
Number of pages	13
Journal	Journal of Organic Chemistry
Volume	78
Issue number	2
DOIs	https://doi.org/10.1021/jo302353g
Publication status	Published - 2013 Jan 18

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo302353g

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title = "Toward the synthesis of phomoidride D",

abstract = "An efficient and highly stereoselective approach toward the phomoidride family of natural products is described. The carbocyclic core structure was assembled using a tandem phenolic oxidation/Diels-Alder cycloaddition and a tandem 5-exo-trig/5-exo-trig radical cyclization to deliver an isotwistane intermediate that, upon a late-stage xanthate-initiated Grob fragmentation, furnishes the requisite bicyclo[4.3.1]decene.",

author = "Murphy, {Graham K.} and Tatsuya Shirahata and Naoto Hama and Aaron Bedermann and Ping Dong and McMahon, {Travis C.} and Twenter, {Barry M.} and Spiegel, {David A.} and McDonald, {Ivar M.} and Nobuaki Taniguchi and Munenori Inoue and Wood, {John L.}",

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doi = "10.1021/jo302353g",

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T1 - Toward the synthesis of phomoidride D

AU - Murphy, Graham K.

AU - Shirahata, Tatsuya

AU - Hama, Naoto

AU - Bedermann, Aaron

AU - Dong, Ping

AU - McMahon, Travis C.

AU - Twenter, Barry M.

AU - Spiegel, David A.

AU - McDonald, Ivar M.

AU - Taniguchi, Nobuaki

AU - Inoue, Munenori

AU - Wood, John L.

PY - 2013/1/18

Y1 - 2013/1/18

N2 - An efficient and highly stereoselective approach toward the phomoidride family of natural products is described. The carbocyclic core structure was assembled using a tandem phenolic oxidation/Diels-Alder cycloaddition and a tandem 5-exo-trig/5-exo-trig radical cyclization to deliver an isotwistane intermediate that, upon a late-stage xanthate-initiated Grob fragmentation, furnishes the requisite bicyclo[4.3.1]decene.

AB - An efficient and highly stereoselective approach toward the phomoidride family of natural products is described. The carbocyclic core structure was assembled using a tandem phenolic oxidation/Diels-Alder cycloaddition and a tandem 5-exo-trig/5-exo-trig radical cyclization to deliver an isotwistane intermediate that, upon a late-stage xanthate-initiated Grob fragmentation, furnishes the requisite bicyclo[4.3.1]decene.

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SP - 477

EP - 489

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 2

ER -

Toward the synthesis of phomoidride D

Abstract

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