Total synthesis of vinigrol

Qingliang Yang, Jon T Njardarson, Cristian Draghici, Fang Li

Research output: Contribution to journalArticle

48 Citations (Scopus)

Abstract

Carbocyclic cage fight: The substrate-controlled total synthesis of vinigrol features a strategic oxidative dearomatization/Diels-Alder cycloaddition reaction and a subsequent palladium-catalyzed cyclization cascade to construct the carbocyclic core. The C4, C9, and C12 stereocenters were installed using either reduction or oxidation reactions, and the diterpenoid core was unraveled by a ring fragmentation reaction.

Original languageEnglish (US)
Pages (from-to)8648-8651
Number of pages4
JournalAngewandte Chemie - International Edition
Volume52
Issue number33
DOIs
StatePublished - Aug 12 2013

Fingerprint

Cycloaddition
Diterpenes
Cyclization
Palladium
Oxidation
Substrates
vinigrol

Keywords

  • dearomatization
  • hydrogenation
  • natural products
  • terpenoids
  • total synthesis

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

Total synthesis of vinigrol. / Yang, Qingliang; Njardarson, Jon T; Draghici, Cristian; Li, Fang.

In: Angewandte Chemie - International Edition, Vol. 52, No. 33, 12.08.2013, p. 8648-8651.

Research output: Contribution to journalArticle

Yang, Qingliang ; Njardarson, Jon T ; Draghici, Cristian ; Li, Fang. / Total synthesis of vinigrol. In: Angewandte Chemie - International Edition. 2013 ; Vol. 52, No. 33. pp. 8648-8651.
@article{3dfed4a2b6f64240ac51a3b02600d093,
title = "Total synthesis of vinigrol",
abstract = "Carbocyclic cage fight: The substrate-controlled total synthesis of vinigrol features a strategic oxidative dearomatization/Diels-Alder cycloaddition reaction and a subsequent palladium-catalyzed cyclization cascade to construct the carbocyclic core. The C4, C9, and C12 stereocenters were installed using either reduction or oxidation reactions, and the diterpenoid core was unraveled by a ring fragmentation reaction.",
keywords = "dearomatization, hydrogenation, natural products, terpenoids, total synthesis",
author = "Qingliang Yang and Njardarson, {Jon T} and Cristian Draghici and Fang Li",
year = "2013",
month = "8",
day = "12",
doi = "10.1002/anie.201304624",
language = "English (US)",
volume = "52",
pages = "8648--8651",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "33",

}

TY - JOUR

T1 - Total synthesis of vinigrol

AU - Yang, Qingliang

AU - Njardarson, Jon T

AU - Draghici, Cristian

AU - Li, Fang

PY - 2013/8/12

Y1 - 2013/8/12

N2 - Carbocyclic cage fight: The substrate-controlled total synthesis of vinigrol features a strategic oxidative dearomatization/Diels-Alder cycloaddition reaction and a subsequent palladium-catalyzed cyclization cascade to construct the carbocyclic core. The C4, C9, and C12 stereocenters were installed using either reduction or oxidation reactions, and the diterpenoid core was unraveled by a ring fragmentation reaction.

AB - Carbocyclic cage fight: The substrate-controlled total synthesis of vinigrol features a strategic oxidative dearomatization/Diels-Alder cycloaddition reaction and a subsequent palladium-catalyzed cyclization cascade to construct the carbocyclic core. The C4, C9, and C12 stereocenters were installed using either reduction or oxidation reactions, and the diterpenoid core was unraveled by a ring fragmentation reaction.

KW - dearomatization

KW - hydrogenation

KW - natural products

KW - terpenoids

KW - total synthesis

UR - http://www.scopus.com/inward/record.url?scp=84882337111&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84882337111&partnerID=8YFLogxK

U2 - 10.1002/anie.201304624

DO - 10.1002/anie.201304624

M3 - Article

C2 - 23818094

AN - SCOPUS:84882337111

VL - 52

SP - 8648

EP - 8651

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 33

ER -