Total Synthesis of (±)-Phomoidride D

Joyce C. Leung; Aaron A. Bedermann; Jón T. Njardarson; David A. Spiegel; Graham K. Murphy; Naoto Hama; Barry M. Twenter; Ping Dong; Tatsuya Shirahata; Ivar M. McDonald; Munenori Inoue; Nobuaki Taniguchi; Travis C. McMahon; Christopher M. Schneider; Nancy Tao; Brian M. Stoltz; John L. Wood

doi:10.1002/anie.201712369

Total Synthesis of (±)-Phomoidride D

Joyce C. Leung, Aaron A. Bedermann, Jón T. Njardarson, David A. Spiegel, Graham K. Murphy, Naoto Hama, Barry M. Twenter, Ping Dong, Tatsuya Shirahata, Ivar M. McDonald, Munenori Inoue, Nobuaki Taniguchi, Travis C. McMahon, Christopher M. Schneider, Nancy Tao, Brian M. Stoltz, John L. Wood

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29 Scopus citations

Abstract

Described herein is a synthetic strategy for the total synthesis of (±)-phomoidride D. This highly efficient and stereoselective approach provides rapid assembly of the carbocyclic core by way of a tandem phenolic oxidation/intramolecular Diels–Alder cycloaddition. A subsequent SmI₂-mediated cyclization cascade delivers an isotwistane intermediate poised for a Wharton fragmentation that unveils the requisite bicyclo[4.3.1]decene skeleton and sets the stage for synthesis completion.

Original language	English (US)
Pages (from-to)	1991-1994
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	57
Issue number	7
DOIs	https://doi.org/10.1002/anie.201712369
State	Published - Feb 12 2018

Keywords

bicyclic compounds
cycloaddition
natural products
oxidation
total synthesis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201712369

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Leung, J. C., Bedermann, A. A., Njardarson, J. T., Spiegel, D. A., Murphy, G. K., Hama, N., Twenter, B. M., Dong, P., Shirahata, T., McDonald, I. M., Inoue, M., Taniguchi, N., McMahon, T. C., Schneider, C. M., Tao, N., Stoltz, B. M., & Wood, J. L. (2018). Total Synthesis of (±)-Phomoidride D. Angewandte Chemie - International Edition, 57(7), 1991-1994. https://doi.org/10.1002/anie.201712369

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abstract = "Described herein is a synthetic strategy for the total synthesis of (±)-phomoidride D. This highly efficient and stereoselective approach provides rapid assembly of the carbocyclic core by way of a tandem phenolic oxidation/intramolecular Diels–Alder cycloaddition. A subsequent SmI2-mediated cyclization cascade delivers an isotwistane intermediate poised for a Wharton fragmentation that unveils the requisite bicyclo[4.3.1]decene skeleton and sets the stage for synthesis completion.",

keywords = "bicyclic compounds, cycloaddition, natural products, oxidation, total synthesis",

author = "Leung, {Joyce C.} and Bedermann, {Aaron A.} and Njardarson, {J{\'o}n T.} and Spiegel, {David A.} and Murphy, {Graham K.} and Naoto Hama and Twenter, {Barry M.} and Ping Dong and Tatsuya Shirahata and McDonald, {Ivar M.} and Munenori Inoue and Nobuaki Taniguchi and McMahon, {Travis C.} and Schneider, {Christopher M.} and Nancy Tao and Stoltz, {Brian M.} and Wood, {John L.}",

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AU - Leung, Joyce C.

AU - Bedermann, Aaron A.

AU - Njardarson, Jón T.

AU - Spiegel, David A.

AU - Murphy, Graham K.

AU - Hama, Naoto

AU - Twenter, Barry M.

AU - Dong, Ping

AU - Shirahata, Tatsuya

AU - McDonald, Ivar M.

AU - Inoue, Munenori

AU - Taniguchi, Nobuaki

AU - McMahon, Travis C.

AU - Schneider, Christopher M.

AU - Tao, Nancy

AU - Stoltz, Brian M.

AU - Wood, John L.

PY - 2018/2/12

Y1 - 2018/2/12

N2 - Described herein is a synthetic strategy for the total synthesis of (±)-phomoidride D. This highly efficient and stereoselective approach provides rapid assembly of the carbocyclic core by way of a tandem phenolic oxidation/intramolecular Diels–Alder cycloaddition. A subsequent SmI2-mediated cyclization cascade delivers an isotwistane intermediate poised for a Wharton fragmentation that unveils the requisite bicyclo[4.3.1]decene skeleton and sets the stage for synthesis completion.

AB - Described herein is a synthetic strategy for the total synthesis of (±)-phomoidride D. This highly efficient and stereoselective approach provides rapid assembly of the carbocyclic core by way of a tandem phenolic oxidation/intramolecular Diels–Alder cycloaddition. A subsequent SmI2-mediated cyclization cascade delivers an isotwistane intermediate poised for a Wharton fragmentation that unveils the requisite bicyclo[4.3.1]decene skeleton and sets the stage for synthesis completion.

KW - bicyclic compounds

KW - cycloaddition

KW - natural products

KW - oxidation

KW - total synthesis

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DO - 10.1002/anie.201712369

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C2 - 29286556

SN - 1433-7851

VL - 57

SP - 1991

EP - 1994

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 7

ER -

Total Synthesis of (±)-Phomoidride D

Abstract

Keywords

ASJC Scopus subject areas

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