Total synthesis of vinigrol

Qingliang Yang; Jon T. Njardarson; Cristian Draghici; Fang Li

doi:10.1002/anie.201304624

Total synthesis of vinigrol

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

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

68 Scopus citations

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 language	English (US)
Pages (from-to)	8648-8651
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	33
DOIs	https://doi.org/10.1002/anie.201304624
State	Published - Aug 12 2013
Externally published	Yes

Keywords

dearomatization
hydrogenation
natural products
terpenoids
total synthesis

ASJC Scopus subject areas

Catalysis
General Chemistry

Access to Document

10.1002/anie.201304624

Cite this

@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 = aug,

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 - https://www.scopus.com/pages/publications/84882337111

UR - https://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

SN - 1433-7851

VL - 52

SP - 8648

EP - 8651

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 33

ER -

Total synthesis of vinigrol

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this