The Vinylogous Mukaiyama Aldol Reaction in Natural Product Synthesis

Research output: Chapter in book/report/conference proceedingContribution to book/anthologyResearchpeer review

View graph of relations

Details

Original languageEnglish
Title of host publicationModern Methods in Stereoselective Aldol Reactions
PublisherWiley-VCH Verlag
Pages83-154
Number of pages72
ISBN (print)9783527332052
Publication statusPublished - 6 Feb 2013

Abstract

The aldol reaction is one of the most predominantly used reactions for the formation of C-C bonds in synthetic organic chemistry. The vinylogous extension of this fundamental C-C bond-forming reaction, the VMAR, is unique in its atomic economy in the generation of hydroxycarbonyl compounds. The generation of the same hydroxycarbonyl compounds via other routes is sometimes cumbersome and often requires multi-step synthetic sequences. Therefore, the VMAR can be a powerful alternative to other strategies in the rational design of polyketide fragments of complex natural products. In this chapter, recent advances in the VMAR and its applications to natural product synthesis are discussed.

Keywords

    Asymmetric, Butenolides, D4 donors, Diastereoselective, Enantioselective, Natural product synthesis, Polyketides, Vinylogous Mukaiyama aldol reaction, Vinylogy

ASJC Scopus subject areas

Cite this

The Vinylogous Mukaiyama Aldol Reaction in Natural Product Synthesis. / Cordes, Martin; Kalesse, Markus.
Modern Methods in Stereoselective Aldol Reactions. Wiley-VCH Verlag, 2013. p. 83-154.

Research output: Chapter in book/report/conference proceedingContribution to book/anthologyResearchpeer review

Cordes, M & Kalesse, M 2013, The Vinylogous Mukaiyama Aldol Reaction in Natural Product Synthesis. in Modern Methods in Stereoselective Aldol Reactions. Wiley-VCH Verlag, pp. 83-154. https://doi.org/10.1002/9783527656714.ch2
Cordes, M., & Kalesse, M. (2013). The Vinylogous Mukaiyama Aldol Reaction in Natural Product Synthesis. In Modern Methods in Stereoselective Aldol Reactions (pp. 83-154). Wiley-VCH Verlag. https://doi.org/10.1002/9783527656714.ch2
Cordes M, Kalesse M. The Vinylogous Mukaiyama Aldol Reaction in Natural Product Synthesis. In Modern Methods in Stereoselective Aldol Reactions. Wiley-VCH Verlag. 2013. p. 83-154 doi: 10.1002/9783527656714.ch2
Cordes, Martin ; Kalesse, Markus. / The Vinylogous Mukaiyama Aldol Reaction in Natural Product Synthesis. Modern Methods in Stereoselective Aldol Reactions. Wiley-VCH Verlag, 2013. pp. 83-154
Download
@inbook{c93b3494c9e444d084d01bd2b5d66150,
title = "The Vinylogous Mukaiyama Aldol Reaction in Natural Product Synthesis",
abstract = "The aldol reaction is one of the most predominantly used reactions for the formation of C-C bonds in synthetic organic chemistry. The vinylogous extension of this fundamental C-C bond-forming reaction, the VMAR, is unique in its atomic economy in the generation of hydroxycarbonyl compounds. The generation of the same hydroxycarbonyl compounds via other routes is sometimes cumbersome and often requires multi-step synthetic sequences. Therefore, the VMAR can be a powerful alternative to other strategies in the rational design of polyketide fragments of complex natural products. In this chapter, recent advances in the VMAR and its applications to natural product synthesis are discussed.",
keywords = "Asymmetric, Butenolides, D4 donors, Diastereoselective, Enantioselective, Natural product synthesis, Polyketides, Vinylogous Mukaiyama aldol reaction, Vinylogy",
author = "Martin Cordes and Markus Kalesse",
year = "2013",
month = feb,
day = "6",
doi = "10.1002/9783527656714.ch2",
language = "English",
isbn = "9783527332052",
pages = "83--154",
booktitle = "Modern Methods in Stereoselective Aldol Reactions",
publisher = "Wiley-VCH Verlag",
address = "Germany",

}

Download

TY - CHAP

T1 - The Vinylogous Mukaiyama Aldol Reaction in Natural Product Synthesis

AU - Cordes, Martin

AU - Kalesse, Markus

PY - 2013/2/6

Y1 - 2013/2/6

N2 - The aldol reaction is one of the most predominantly used reactions for the formation of C-C bonds in synthetic organic chemistry. The vinylogous extension of this fundamental C-C bond-forming reaction, the VMAR, is unique in its atomic economy in the generation of hydroxycarbonyl compounds. The generation of the same hydroxycarbonyl compounds via other routes is sometimes cumbersome and often requires multi-step synthetic sequences. Therefore, the VMAR can be a powerful alternative to other strategies in the rational design of polyketide fragments of complex natural products. In this chapter, recent advances in the VMAR and its applications to natural product synthesis are discussed.

AB - The aldol reaction is one of the most predominantly used reactions for the formation of C-C bonds in synthetic organic chemistry. The vinylogous extension of this fundamental C-C bond-forming reaction, the VMAR, is unique in its atomic economy in the generation of hydroxycarbonyl compounds. The generation of the same hydroxycarbonyl compounds via other routes is sometimes cumbersome and often requires multi-step synthetic sequences. Therefore, the VMAR can be a powerful alternative to other strategies in the rational design of polyketide fragments of complex natural products. In this chapter, recent advances in the VMAR and its applications to natural product synthesis are discussed.

KW - Asymmetric

KW - Butenolides

KW - D4 donors

KW - Diastereoselective

KW - Enantioselective

KW - Natural product synthesis

KW - Polyketides

KW - Vinylogous Mukaiyama aldol reaction

KW - Vinylogy

UR - http://www.scopus.com/inward/record.url?scp=84885719656&partnerID=8YFLogxK

U2 - 10.1002/9783527656714.ch2

DO - 10.1002/9783527656714.ch2

M3 - Contribution to book/anthology

AN - SCOPUS:84885719656

SN - 9783527332052

SP - 83

EP - 154

BT - Modern Methods in Stereoselective Aldol Reactions

PB - Wiley-VCH Verlag

ER -

By the same author(s)