Total Synthesis of the Marine Polyketide (-)-Gracilioether F

Ritabrata Datta; Subrata Ghosh

doi:10.1021/acs.joc.7b01179

Total Synthesis of the Marine Polyketide (-)-Gracilioether F

Ritabrata Datta
, Subrata Ghosh

Immunology and Immunotherapy

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

8 Citations (Scopus)

Abstract

First asymmetric synthesis of the marine natural product (-)-gracilioether F is described from a d-mannitol derived known compound. The key step involves intramolecular 1,4-conjugate addition of a hydroxymethyl radical generated from Ti (III) mediated ring opening of a terminal epoxy ring tethered to a butenolide to produce stereoselectively a five-membered ring fused bicyclic lactone, the core structure present in gracilioether F.

Original language	English
Pages (from-to)	7675-7682
Number of pages	8
Journal	The Journal of Organic Chemistry
Volume	82
Issue number	14
DOIs	https://doi.org/10.1021/acs.joc.7b01179
Publication status	Published - 21 Jun 2017

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 14 Life Below Water

Keywords

Journal Article

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http://pubs.acs.org/doi/10.1021/acs.joc.7b01179Licence: None: All rights reserved

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abstract = "First asymmetric synthesis of the marine natural product (-)-gracilioether F is described from a d-mannitol derived known compound. The key step involves intramolecular 1,4-conjugate addition of a hydroxymethyl radical generated from Ti (III) mediated ring opening of a terminal epoxy ring tethered to a butenolide to produce stereoselectively a five-membered ring fused bicyclic lactone, the core structure present in gracilioether F.",

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AU - Ghosh, Subrata

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N2 - First asymmetric synthesis of the marine natural product (-)-gracilioether F is described from a d-mannitol derived known compound. The key step involves intramolecular 1,4-conjugate addition of a hydroxymethyl radical generated from Ti (III) mediated ring opening of a terminal epoxy ring tethered to a butenolide to produce stereoselectively a five-membered ring fused bicyclic lactone, the core structure present in gracilioether F.

AB - First asymmetric synthesis of the marine natural product (-)-gracilioether F is described from a d-mannitol derived known compound. The key step involves intramolecular 1,4-conjugate addition of a hydroxymethyl radical generated from Ti (III) mediated ring opening of a terminal epoxy ring tethered to a butenolide to produce stereoselectively a five-membered ring fused bicyclic lactone, the core structure present in gracilioether F.

KW - Journal Article

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DO - 10.1021/acs.joc.7b01179

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EP - 7682

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 14

ER -

Total Synthesis of the Marine Polyketide (-)-Gracilioether F

Abstract

UN SDGs

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