The Use of Butane Diacetals of Glycolic Acid as Precursors for the Synthesis of the Phytotoxic Calmodulin Inhibitor Herbarumin II

Elena Díez; Darren J. Dixon; Steven V. Ley; Alessandra Polara; Felix Rodríguez

doi:10.1002/hlca.200390314

The Use of Butane Diacetals of Glycolic Acid as Precursors for the Synthesis of the Phytotoxic Calmodulin Inhibitor Herbarumin II

Elena Díez, Darren J. Dixon, Steven V. Ley, Alessandra Polara, Felix Rodríguez

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

Abstract

The total synthesis of phytotoxic nonenolide herbarumin II (1) has been achieved by implementation of butane diacetal (BDA)-desymmetrised glycolate building blocks. Three of the four stereogenic centres present in the key coupling fragments were generated from both enantiomeric forms of the BDA building block in highly diastereoselective alkylation and aldol reactions.

Original language	English
Pages (from-to)	3717-3729
Number of pages	12
Journal	Helvetica Chimica Acta
Volume	86
Issue number	11
DOIs	https://doi.org/10.1002/hlca.200390314
Publication status	Published - 2003

Keywords

Crystal structure; Molecular structure (of herbarumin II); Asymmetric synthesis and induction; Cyclization; Metathesis (prepn. of herbarumin II from glycolate building blocks via ring closing metathesis, and diastereoselective alkylation and aldol reactions); Aldol condensation; Alkylation (stereoselective; prepn. of herbarumin II from glycolate building blocks via ring closing metathesis, and diastereoselective alkylation and aldol reactions)

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10.1002/hlca.200390314

CCDC 217165: Experimental Crystal Structure Determination
Díez, E. (Contributor), Dixon, D. (Contributor), Ley, S. V. (Contributor), Polara, A. (Contributor) & Rodríguez, F. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2004
DOI: 10.5517/cc78zbs, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc78zbs&sid=DataCite
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title = "The Use of Butane Diacetals of Glycolic Acid as Precursors for the Synthesis of the Phytotoxic Calmodulin Inhibitor Herbarumin II",

abstract = "The total synthesis of phytotoxic nonenolide herbarumin II (1) has been achieved by implementation of butane diacetal (BDA)-desymmetrised glycolate building blocks. Three of the four stereogenic centres present in the key coupling fragments were generated from both enantiomeric forms of the BDA building block in highly diastereoselective alkylation and aldol reactions.",

keywords = "Crystal structure; Molecular structure (of herbarumin II); Asymmetric synthesis and induction; Cyclization; Metathesis (prepn. of herbarumin II from glycolate building blocks via ring closing metathesis, and diastereoselective alkylation and aldol reactions); Aldol condensation; Alkylation (stereoselective; prepn. of herbarumin II from glycolate building blocks via ring closing metathesis, and diastereoselective alkylation and aldol reactions)",

author = "Elena D{\'i}ez and Dixon, {Darren J.} and Ley, {Steven V.} and Alessandra Polara and Felix Rodr{\'i}guez",

year = "2003",

doi = "10.1002/hlca.200390314",

language = "English",

volume = "86",

pages = "3717--3729",

journal = "Helvetica Chimica Acta",

issn = "1522-2675",

publisher = "John Wiley & Sons Ltd",

number = "11",

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T1 - The Use of Butane Diacetals of Glycolic Acid as Precursors for the Synthesis of the Phytotoxic Calmodulin Inhibitor Herbarumin II

AU - Díez, Elena

AU - Dixon, Darren J.

AU - Ley, Steven V.

AU - Polara, Alessandra

AU - Rodríguez, Felix

PY - 2003

Y1 - 2003

N2 - The total synthesis of phytotoxic nonenolide herbarumin II (1) has been achieved by implementation of butane diacetal (BDA)-desymmetrised glycolate building blocks. Three of the four stereogenic centres present in the key coupling fragments were generated from both enantiomeric forms of the BDA building block in highly diastereoselective alkylation and aldol reactions.

AB - The total synthesis of phytotoxic nonenolide herbarumin II (1) has been achieved by implementation of butane diacetal (BDA)-desymmetrised glycolate building blocks. Three of the four stereogenic centres present in the key coupling fragments were generated from both enantiomeric forms of the BDA building block in highly diastereoselective alkylation and aldol reactions.

KW - Crystal structure; Molecular structure (of herbarumin II); Asymmetric synthesis and induction; Cyclization; Metathesis (prepn. of herbarumin II from glycolate building blocks via ring closing metathesis, and diastereoselective alkylation and aldol reactio

U2 - 10.1002/hlca.200390314

DO - 10.1002/hlca.200390314

M3 - Article

SN - 1522-2675

VL - 86

SP - 3717

EP - 3729

JO - Helvetica Chimica Acta

JF - Helvetica Chimica Acta

IS - 11

ER -

The Use of Butane Diacetals of Glycolic Acid as Precursors for the Synthesis of the Phytotoxic Calmodulin Inhibitor Herbarumin II

Abstract

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CCDC 217165: Experimental Crystal Structure Determination

Cite this