Short Stereoselective Synthesis of the Phytophthora Universal Mating Hormone alpha 1 Using Lithiation/Borylation Reactions

Alexander P. Pulis; Philipp Fackler; Varinder K. Aggarwal

doi:10.1002/anie.201400714

Short Stereoselective Synthesis of the Phytophthora Universal Mating Hormone alpha 1 Using Lithiation/Borylation Reactions

Alexander P. Pulis, Philipp Fackler, Varinder K. Aggarwal^*

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

16 Citations (Scopus)

323 Downloads (Pure)

Abstract

The universal mating hormone 1 of the virulent plant pathogen Phytophthora has been synthesized in 12 steps and 28% overall yield. Key CC bond-forming steps involved the use of two lithiation/borylation reactions to couple together enantioenriched building blocks, one of which also set up the stereochemistry of the tertiary alcohol at C11. Detailed analysis showed that the diastereomeric purity of the target molecule was >91%, the highest obtained to date.

Original language	English
Pages (from-to)	4382-4385
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	53
Issue number	17
DOIs	https://doi.org/10.1002/anie.201400714
Publication status	Published - 22 Apr 2014

Keywords

asymmetric synthesis
boron
lithium
natural products
total synthesis
4 STEREOISOMERS
BORONIC ESTERS
ALPHA-1
BORANES

Access to Document

10.1002/anie.201400714

APulis_ACIE_2014
This is the pre-peer reviewed version of the following article: Pulis, A. P., Fackler, P. and Aggarwal, V. K. (2014), Short Stereoselective Synthesis of the Phytophthora Universal Mating Hormone α1 Using Lithiation/Borylation Reactions. Angew. Chem. Int. Ed., 53: 4382–4385. doi: 10.1002/anie.201400714, which has been published in final form at http://onlinelibrary.wiley.com/doi/10.1002/anie.201400714/abstract
Accepted author manuscript, 329 KB

http://onlinelibrary.wiley.com/doi/10.1002/anie.201400714/abstract

2 Finished

3-month Core Capability for Chemistry Research
Crosby, J.
1/01/13 → 1/04/13
Project: Research
Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis
Aggarwal, V. K.
14/05/12 → 13/01/18
Project: Research

Professor Varinder K Aggarwal
- V.Aggarwal@bristol.ac.uk
- School of Chemistry - Alfred Capper Pass Chair of Chemistry
- Synthesis
- Supramolecular and Mechanistic Chemistry
- Catalysis
Person: Academic , Member

Cite this

@article{908c7ce16e3147a996cd6b19cb982314,

title = "Short Stereoselective Synthesis of the Phytophthora Universal Mating Hormone alpha 1 Using Lithiation/Borylation Reactions",

abstract = "The universal mating hormone 1 of the virulent plant pathogen Phytophthora has been synthesized in 12 steps and 28% overall yield. Key CC bond-forming steps involved the use of two lithiation/borylation reactions to couple together enantioenriched building blocks, one of which also set up the stereochemistry of the tertiary alcohol at C11. Detailed analysis showed that the diastereomeric purity of the target molecule was >91%, the highest obtained to date.",

keywords = "asymmetric synthesis, boron, lithium, natural products, total synthesis, 4 STEREOISOMERS, BORONIC ESTERS, ALPHA-1, BORANES",

author = "Pulis, {Alexander P.} and Philipp Fackler and Aggarwal, {Varinder K.}",

year = "2014",

month = apr,

day = "22",

doi = "10.1002/anie.201400714",

language = "English",

volume = "53",

pages = "4382--4385",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "Wiley-VCH Verlag",

number = "17",

}

TY - JOUR

T1 - Short Stereoselective Synthesis of the Phytophthora Universal Mating Hormone alpha 1 Using Lithiation/Borylation Reactions

AU - Pulis, Alexander P.

AU - Fackler, Philipp

AU - Aggarwal, Varinder K.

PY - 2014/4/22

Y1 - 2014/4/22

N2 - The universal mating hormone 1 of the virulent plant pathogen Phytophthora has been synthesized in 12 steps and 28% overall yield. Key CC bond-forming steps involved the use of two lithiation/borylation reactions to couple together enantioenriched building blocks, one of which also set up the stereochemistry of the tertiary alcohol at C11. Detailed analysis showed that the diastereomeric purity of the target molecule was >91%, the highest obtained to date.

AB - The universal mating hormone 1 of the virulent plant pathogen Phytophthora has been synthesized in 12 steps and 28% overall yield. Key CC bond-forming steps involved the use of two lithiation/borylation reactions to couple together enantioenriched building blocks, one of which also set up the stereochemistry of the tertiary alcohol at C11. Detailed analysis showed that the diastereomeric purity of the target molecule was >91%, the highest obtained to date.

KW - asymmetric synthesis

KW - boron

KW - lithium

KW - natural products

KW - total synthesis

KW - 4 STEREOISOMERS

KW - BORONIC ESTERS

KW - ALPHA-1

KW - BORANES

U2 - 10.1002/anie.201400714

DO - 10.1002/anie.201400714

M3 - Article (Academic Journal)

C2 - 24634275

VL - 53

SP - 4382

EP - 4385

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 17

ER -

Short Stereoselective Synthesis of the Phytophthora Universal Mating Hormone alpha 1 Using Lithiation/Borylation Reactions

Abstract

Keywords

Access to Document

3-month Core Capability for Chemistry Research

Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis

Professor Varinder K Aggarwal

Cite this