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

Keywords

Journal Article

UN SDGs

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

Access to Document

10.1021/acs.joc.7b01179Licence: None: All rights reserved

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

Cite this

@article{5b6d2e15d1ac4b979ebe20267214a455,

title = "Total Synthesis of the Marine Polyketide (-)-Gracilioether F",

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.",

keywords = "Journal Article",

author = "Ritabrata Datta and Subrata Ghosh",

year = "2017",

month = jun,

day = "21",

doi = "10.1021/acs.joc.7b01179",

language = "English",

volume = "82",

pages = "7675--7682",

journal = "The Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "14",

}

TY - JOUR

T1 - Total Synthesis of the Marine Polyketide (-)-Gracilioether F

AU - Datta, Ritabrata

AU - Ghosh, Subrata

PY - 2017/6/21

Y1 - 2017/6/21

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

U2 - 10.1021/acs.joc.7b01179

DO - 10.1021/acs.joc.7b01179

M3 - Article

C2 - 28636373

SN - 0022-3263

VL - 82

SP - 7675

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

Keywords

UN SDGs

Access to Document

Fingerprint

Cite this