Synthesis of the C9-C21 fragment of geldanamycin via a diastereoselective substrate-controlled hydrogenation

Tony Horneff; Thorsten Bach

doi:10.1055/s-0028-1083625

Synthesis of the C9-C21 fragment of geldanamycin via a diastereoselective substrate-controlled hydrogenation

Tony Horneff
, Thorsten Bach

Chair of Organic Chemistry 1

Technical University of Munich
Scripps Research Institute

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

4 Scopus citations

Abstract

An Ir-catalyzed diastereoselective hydrogenation was employed to establish the stereogenic center at carbon atom C14 of a C9-C21 fragment of geldanamycin. The fragment was stereoselectively synthesized from D-mannitol in 18 steps.

Original language	English
Pages (from-to)	2969-2972
Number of pages	4
Journal	Synlett
Issue number	19
DOIs	https://doi.org/10.1055/s-0028-1083625
State	Published - 1 Dec 2008

Keywords

Ansamycins
Diastereoselectivity
Hydrogenation
Protecting groups
Quinones
Stereoselective synthesis

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10.1055/s-0028-1083625

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title = "Synthesis of the C9-C21 fragment of geldanamycin via a diastereoselective substrate-controlled hydrogenation",

abstract = "An Ir-catalyzed diastereoselective hydrogenation was employed to establish the stereogenic center at carbon atom C14 of a C9-C21 fragment of geldanamycin. The fragment was stereoselectively synthesized from D-mannitol in 18 steps.",

keywords = "Ansamycins, Diastereoselectivity, Hydrogenation, Protecting groups, Quinones, Stereoselective synthesis",

author = "Tony Horneff and Thorsten Bach",

year = "2008",

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doi = "10.1055/s-0028-1083625",

language = "English",

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journal = "Synlett",

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T1 - Synthesis of the C9-C21 fragment of geldanamycin via a diastereoselective substrate-controlled hydrogenation

AU - Horneff, Tony

AU - Bach, Thorsten

PY - 2008/12/1

Y1 - 2008/12/1

N2 - An Ir-catalyzed diastereoselective hydrogenation was employed to establish the stereogenic center at carbon atom C14 of a C9-C21 fragment of geldanamycin. The fragment was stereoselectively synthesized from D-mannitol in 18 steps.

AB - An Ir-catalyzed diastereoselective hydrogenation was employed to establish the stereogenic center at carbon atom C14 of a C9-C21 fragment of geldanamycin. The fragment was stereoselectively synthesized from D-mannitol in 18 steps.

KW - Ansamycins

KW - Diastereoselectivity

KW - Hydrogenation

KW - Protecting groups

KW - Quinones

KW - Stereoselective synthesis

UR - https://www.scopus.com/pages/publications/57649114606

U2 - 10.1055/s-0028-1083625

DO - 10.1055/s-0028-1083625

M3 - Article

AN - SCOPUS:57649114606

SN - 0936-5214

SP - 2969

EP - 2972

JO - Synlett

JF - Synlett

IS - 19

ER -

Synthesis of the C9-C21 fragment of geldanamycin via a diastereoselective substrate-controlled hydrogenation

Abstract

Keywords

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