2.9 Chiral Pool Synthesis: Chiral Pool Syntheses from cis-Cyclohexadiene Diols

U. Rinner

doi:10.1016/B978-0-08-095167-6.00219-6

2.9 Chiral Pool Synthesis: Chiral Pool Syntheses from cis-Cyclohexadiene Diols

U. Rinner^*

^*Corresponding author for this work

Research output: Chapter in Book/Report/Conference proceeding › Chapter

26 Citations (SciVal)

Abstract

Cyclohexadiene diols have been used extensively in the diastereoselective preparation of various natural products. These highly versatile chiral synthons, easily obtained by whole cell oxidation of aromatic substrates by soil bacteria, allow a huge variety of possible functional group manipulations and interconversions. In this chapter, the inherent advantages of cis-cyclohexadiene diols for synthesis are outlined. Subsequently, different diastereoselective reactions and reaction sequences with cis-cyclohexadiene diols are discussed along with selected applications in the area of natural product synthesis.

Original language	English
Title of host publication	Synthetic Methods I - Chiral Pool and Diastereoselective Methods
Publisher	Elsevier Ltd
Pages	240-267
Number of pages	28
Volume	2
ISBN (Print)	9780080951683
DOIs	https://doi.org/10.1016/B978-0-08-095167-6.00219-6
Publication status	Published - Sept 2012
Externally published	Yes

Keywords

Aziridination
Cyclohexadiene diols
Dihydroxylation
Epoxidation
Total synthesis

ASJC Scopus subject areas

General Chemistry

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10.1016/B978-0-08-095167-6.00219-6

Cite this

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title = "2.9 Chiral Pool Synthesis: Chiral Pool Syntheses from cis-Cyclohexadiene Diols",

abstract = "Cyclohexadiene diols have been used extensively in the diastereoselective preparation of various natural products. These highly versatile chiral synthons, easily obtained by whole cell oxidation of aromatic substrates by soil bacteria, allow a huge variety of possible functional group manipulations and interconversions. In this chapter, the inherent advantages of cis-cyclohexadiene diols for synthesis are outlined. Subsequently, different diastereoselective reactions and reaction sequences with cis-cyclohexadiene diols are discussed along with selected applications in the area of natural product synthesis.",

keywords = "Aziridination, Cyclohexadiene diols, Dihydroxylation, Epoxidation, Total synthesis",

author = "U. Rinner",

year = "2012",

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doi = "10.1016/B978-0-08-095167-6.00219-6",

language = "English",

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T1 - 2.9 Chiral Pool Synthesis

T2 - Chiral Pool Syntheses from cis-Cyclohexadiene Diols

AU - Rinner, U.

PY - 2012/9

Y1 - 2012/9

N2 - Cyclohexadiene diols have been used extensively in the diastereoselective preparation of various natural products. These highly versatile chiral synthons, easily obtained by whole cell oxidation of aromatic substrates by soil bacteria, allow a huge variety of possible functional group manipulations and interconversions. In this chapter, the inherent advantages of cis-cyclohexadiene diols for synthesis are outlined. Subsequently, different diastereoselective reactions and reaction sequences with cis-cyclohexadiene diols are discussed along with selected applications in the area of natural product synthesis.

AB - Cyclohexadiene diols have been used extensively in the diastereoselective preparation of various natural products. These highly versatile chiral synthons, easily obtained by whole cell oxidation of aromatic substrates by soil bacteria, allow a huge variety of possible functional group manipulations and interconversions. In this chapter, the inherent advantages of cis-cyclohexadiene diols for synthesis are outlined. Subsequently, different diastereoselective reactions and reaction sequences with cis-cyclohexadiene diols are discussed along with selected applications in the area of natural product synthesis.

KW - Aziridination

KW - Cyclohexadiene diols

KW - Dihydroxylation

KW - Epoxidation

KW - Total synthesis

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AN - SCOPUS:84902435277

SN - 9780080951683

VL - 2

SP - 240

EP - 267

BT - Synthetic Methods I - Chiral Pool and Diastereoselective Methods

PB - Elsevier Ltd

ER -

2.9 Chiral Pool Synthesis: Chiral Pool Syntheses from cis-Cyclohexadiene Diols

Abstract

Keywords

ASJC Scopus subject areas

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