The Catalytic Enantioselective Total Synthesis of (+)‐Liphagal

Joshua J. Day, Ryan M. McFadden, Scott C. Virgil, Helene Kolding, Jennifer L. Alleva, Brian M. Stoltz

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

Ring a ding: The first catalytic enantioselective total synthesis of the meroterpenoid natural product (+)-liphagal is disclosed. The approach showcases a variety of technology including enantioselective enolate alkylation, a photochemical alkyne-alkene [2+2] reaction, microwaveassisted metal catalysis, and an intramolecular aryne capture cyclization reaction. Pivotal to the successful completion of the synthesis was a sequence involving ring expansion from a [6-5-4]
tricycle to a [6-7] bicyclic core followed by stereoselective hydrogenation of a sterically occluded tri-substituted olefin to establish the trans homodecalin system found in the natural product
Original languageEnglish
JournalAngewandte Chemie International Edition
Volume50
Issue number30
Pages (from-to)6814-6818
ISSN1433-7851
DOIs
Publication statusPublished - 2011

Keywords

  • Total synthesis
  • Terpenoids
  • Arynes
  • Asymmetric catalysis
  • Palladium
  • Rearrangement

Cite this

Day, J. J., McFadden, R. M., Virgil, S. C., Kolding, H., Alleva, J. L., & Stoltz, B. M. (2011). The Catalytic Enantioselective Total Synthesis of (+)‐Liphagal. Angewandte Chemie International Edition, 50(30), 6814-6818. https://doi.org/10.1002/anie.201101842
Day, Joshua J. ; McFadden, Ryan M. ; Virgil, Scott C. ; Kolding, Helene ; Alleva, Jennifer L. ; Stoltz, Brian M. / The Catalytic Enantioselective Total Synthesis of (+)‐Liphagal. In: Angewandte Chemie International Edition. 2011 ; Vol. 50, No. 30. pp. 6814-6818.
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abstract = "Ring a ding: The first catalytic enantioselective total synthesis of the meroterpenoid natural product (+)-liphagal is disclosed. The approach showcases a variety of technology including enantioselective enolate alkylation, a photochemical alkyne-alkene [2+2] reaction, microwaveassisted metal catalysis, and an intramolecular aryne capture cyclization reaction. Pivotal to the successful completion of the synthesis was a sequence involving ring expansion from a [6-5-4]tricycle to a [6-7] bicyclic core followed by stereoselective hydrogenation of a sterically occluded tri-substituted olefin to establish the trans homodecalin system found in the natural product",
keywords = "Total synthesis, Terpenoids, Arynes, Asymmetric catalysis, Palladium, Rearrangement",
author = "Day, {Joshua J.} and McFadden, {Ryan M.} and Virgil, {Scott C.} and Helene Kolding and Alleva, {Jennifer L.} and Stoltz, {Brian M.}",
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Day, JJ, McFadden, RM, Virgil, SC, Kolding, H, Alleva, JL & Stoltz, BM 2011, 'The Catalytic Enantioselective Total Synthesis of (+)‐Liphagal', Angewandte Chemie International Edition, vol. 50, no. 30, pp. 6814-6818. https://doi.org/10.1002/anie.201101842

The Catalytic Enantioselective Total Synthesis of (+)‐Liphagal. / Day, Joshua J.; McFadden, Ryan M.; Virgil, Scott C.; Kolding, Helene; Alleva, Jennifer L.; Stoltz, Brian M.

In: Angewandte Chemie International Edition, Vol. 50, No. 30, 2011, p. 6814-6818.

Research output: Contribution to journalJournal articleResearchpeer-review

TY - JOUR

T1 - The Catalytic Enantioselective Total Synthesis of (+)‐Liphagal

AU - Day, Joshua J.

AU - McFadden, Ryan M.

AU - Virgil, Scott C.

AU - Kolding, Helene

AU - Alleva, Jennifer L.

AU - Stoltz, Brian M.

PY - 2011

Y1 - 2011

N2 - Ring a ding: The first catalytic enantioselective total synthesis of the meroterpenoid natural product (+)-liphagal is disclosed. The approach showcases a variety of technology including enantioselective enolate alkylation, a photochemical alkyne-alkene [2+2] reaction, microwaveassisted metal catalysis, and an intramolecular aryne capture cyclization reaction. Pivotal to the successful completion of the synthesis was a sequence involving ring expansion from a [6-5-4]tricycle to a [6-7] bicyclic core followed by stereoselective hydrogenation of a sterically occluded tri-substituted olefin to establish the trans homodecalin system found in the natural product

AB - Ring a ding: The first catalytic enantioselective total synthesis of the meroterpenoid natural product (+)-liphagal is disclosed. The approach showcases a variety of technology including enantioselective enolate alkylation, a photochemical alkyne-alkene [2+2] reaction, microwaveassisted metal catalysis, and an intramolecular aryne capture cyclization reaction. Pivotal to the successful completion of the synthesis was a sequence involving ring expansion from a [6-5-4]tricycle to a [6-7] bicyclic core followed by stereoselective hydrogenation of a sterically occluded tri-substituted olefin to establish the trans homodecalin system found in the natural product

KW - Total synthesis

KW - Terpenoids

KW - Arynes

KW - Asymmetric catalysis

KW - Palladium

KW - Rearrangement

U2 - 10.1002/anie.201101842

DO - 10.1002/anie.201101842

M3 - Journal article

VL - 50

SP - 6814

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JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

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ER -