Silyl Migrations in D-Xylose Derivatives: Total Synthesis of a Marine Quinoline Alkaloid

Anuchit Phanumartwiwath; Tom Hornsby; Joazaizulfazli Jamalis; Christopher D. Bailey; Christine L. Willis

doi:10.1021/ol402760p

Silyl Migrations in D-Xylose Derivatives: Total Synthesis of a Marine Quinoline Alkaloid

Anuchit Phanumartwiwath
, Tom Hornsby
, Joazaizulfazli Jamalis
, Christopher D. Bailey
, Christine L. Willis^*

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

19 Citations (Scopus)

Abstract

A versatile method for the synthesis of orthogonally protected D-xylose 1-thioethers is described using unusual silyl group migrations which were pivotal in the synthesis of 4,8-dimethyl-6-O-(2',4'-di-O-methyl-beta-D-xylopyranosyl)hydroxyquinoline confirming the structure and absolute configuration of the natural product.

Original language	English
Pages (from-to)	5734-5737
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	22
DOIs	https://doi.org/10.1021/ol402760p
Publication status	Published - 15 Nov 2013

UN SDGs

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

SDG 14 Life Below Water

Research Groups and Themes

BCS and TECS CDTs
Organic & Biological

Keywords

ALGA POLYCAVERNOSA-TSUDAI
SPONGE MYRIASTRA-CLAVOSA
CONVENIENT SYNTHESIS
MACROLIDE
ACCEPTOR
ROUTE

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10.1021/ol402760p

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3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research

Cite this

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title = "Silyl Migrations in D-Xylose Derivatives: Total Synthesis of a Marine Quinoline Alkaloid",

abstract = "A versatile method for the synthesis of orthogonally protected D-xylose 1-thioethers is described using unusual silyl group migrations which were pivotal in the synthesis of 4,8-dimethyl-6-O-(2',4'-di-O-methyl-beta-D-xylopyranosyl)hydroxyquinoline confirming the structure and absolute configuration of the natural product.",

keywords = "ALGA POLYCAVERNOSA-TSUDAI, SPONGE MYRIASTRA-CLAVOSA, CONVENIENT SYNTHESIS, MACROLIDE, ACCEPTOR, ROUTE",

author = "Anuchit Phanumartwiwath and Tom Hornsby and Joazaizulfazli Jamalis and Bailey, \{Christopher D.\} and Willis, \{Christine L.\}",

year = "2013",

month = nov,

day = "15",

doi = "10.1021/ol402760p",

language = "English",

volume = "15",

pages = "5734--5737",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "22",

}

TY - JOUR

T1 - Silyl Migrations in D-Xylose Derivatives

T2 - Total Synthesis of a Marine Quinoline Alkaloid

AU - Phanumartwiwath, Anuchit

AU - Hornsby, Tom

AU - Jamalis, Joazaizulfazli

AU - Bailey, Christopher D.

AU - Willis, Christine L.

PY - 2013/11/15

Y1 - 2013/11/15

N2 - A versatile method for the synthesis of orthogonally protected D-xylose 1-thioethers is described using unusual silyl group migrations which were pivotal in the synthesis of 4,8-dimethyl-6-O-(2',4'-di-O-methyl-beta-D-xylopyranosyl)hydroxyquinoline confirming the structure and absolute configuration of the natural product.

AB - A versatile method for the synthesis of orthogonally protected D-xylose 1-thioethers is described using unusual silyl group migrations which were pivotal in the synthesis of 4,8-dimethyl-6-O-(2',4'-di-O-methyl-beta-D-xylopyranosyl)hydroxyquinoline confirming the structure and absolute configuration of the natural product.

KW - ALGA POLYCAVERNOSA-TSUDAI

KW - SPONGE MYRIASTRA-CLAVOSA

KW - CONVENIENT SYNTHESIS

KW - MACROLIDE

KW - ACCEPTOR

KW - ROUTE

U2 - 10.1021/ol402760p

DO - 10.1021/ol402760p

M3 - Article (Academic Journal)

C2 - 24229077

SN - 1523-7060

VL - 15

SP - 5734

EP - 5737

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

Silyl Migrations in D-Xylose Derivatives: Total Synthesis of a Marine Quinoline Alkaloid

Abstract

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Keywords

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3-month Core Capability for Chemistry Research

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