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

10 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

Structured keywords

BCS and TECS CDTs

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.
1/01/13 → 1/04/13
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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",

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doi = "10.1021/ol402760p",

language = "English",

volume = "15",

pages = "5734--5737",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "22",

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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

VL - 15

SP - 5734

EP - 5737

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 22

ER -

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

Abstract

Structured keywords

Keywords

Access to Document

3-month Core Capability for Chemistry Research

Cite this