Total synthesis of kingianinsA, D, and F

Samuel L. Drew; Andrew L. Lawrence; Michael S. Sherburn

doi:10.1002/anie.201210084

Total synthesis of kingianinsA, D, and F

Samuel L. Drew^*, Andrew L. Lawrence, Michael S. Sherburn

^*Corresponding author for this work

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

68 Citations (Scopus)

Abstract

A synthesis fit for a king: The total synthesis of (±)-kingianinsA, D, and F has been achieved in ten steps. Key features include the gram-scale synthesis and partial reduction of a conjugated tetrayne to a (Z,Z,Z,Z)-tetraene, the domino 8π-6π electrocyclic ring closure of a (Z,Z,Z,Z)-tetraene, and the radical-cation-catalyzed formal Diels-Alder dimerization of functionalized bicyclo[4.2.0]octadiene precursors.

Original language	English
Pages (from-to)	4221-4224
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	15
DOIs	https://doi.org/10.1002/anie.201210084
Publication status	Published - 8 Apr 2013

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title = "Total synthesis of kingianinsA, D, and F",

abstract = "A synthesis fit for a king: The total synthesis of (±)-kingianinsA, D, and F has been achieved in ten steps. Key features include the gram-scale synthesis and partial reduction of a conjugated tetrayne to a (Z,Z,Z,Z)-tetraene, the domino 8π-6π electrocyclic ring closure of a (Z,Z,Z,Z)-tetraene, and the radical-cation-catalyzed formal Diels-Alder dimerization of functionalized bicyclo[4.2.0]octadiene precursors.",

keywords = "biomimetic synthesis, domino reactions, natural products, polyynes, radical cations",

author = "Drew, \{Samuel L.\} and Lawrence, \{Andrew L.\} and Sherburn, \{Michael S.\}",

year = "2013",

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doi = "10.1002/anie.201210084",

language = "English",

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journal = "Angewandte Chemie - International Edition",

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T1 - Total synthesis of kingianinsA, D, and F

AU - Drew, Samuel L.

AU - Lawrence, Andrew L.

AU - Sherburn, Michael S.

PY - 2013/4/8

Y1 - 2013/4/8

N2 - A synthesis fit for a king: The total synthesis of (±)-kingianinsA, D, and F has been achieved in ten steps. Key features include the gram-scale synthesis and partial reduction of a conjugated tetrayne to a (Z,Z,Z,Z)-tetraene, the domino 8π-6π electrocyclic ring closure of a (Z,Z,Z,Z)-tetraene, and the radical-cation-catalyzed formal Diels-Alder dimerization of functionalized bicyclo[4.2.0]octadiene precursors.

AB - A synthesis fit for a king: The total synthesis of (±)-kingianinsA, D, and F has been achieved in ten steps. Key features include the gram-scale synthesis and partial reduction of a conjugated tetrayne to a (Z,Z,Z,Z)-tetraene, the domino 8π-6π electrocyclic ring closure of a (Z,Z,Z,Z)-tetraene, and the radical-cation-catalyzed formal Diels-Alder dimerization of functionalized bicyclo[4.2.0]octadiene precursors.

KW - biomimetic synthesis

KW - domino reactions

KW - natural products

KW - polyynes

KW - radical cations

UR - https://www.scopus.com/pages/publications/84875866470

U2 - 10.1002/anie.201210084

DO - 10.1002/anie.201210084

M3 - Article

SN - 1433-7851

VL - 52

SP - 4221

EP - 4224

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 15

ER -

Total synthesis of kingianinsA, D, and F

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