Synthesis of azido analogues of medermycin

Margaret A. Brimble; Roger M. Davey; Malcolm D. McLeod

doi:10.1055/s-2002-32955

Synthesis of azido analogues of medermycin

Margaret A. Brimble^*, Roger M. Davey, Malcolm D. McLeod

^*Corresponding author for this work

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

15 Citations (Scopus)

Abstract

The synthesis of azido analogues 2a,2b of the pyrano-naphthoquinone antibiotic medermycin 1 has been achieved in eight steps from naphthol 8 and azido glycosyl sugar 7 in 9.3% overall yield. Key steps include the direct BF₃·Et₂O promoted C-glycosylation of naphthol 8, introduction of an acetyl group onto a bromonaphthoquinone via Stille coupling with (α-ethoxy-vinyl)tributyltin, furofuran annulation of a naphthoquinone to a furonaphthofuran using 2-trimethylsilyloxyfuran 5 and oxidative rearrangement of a furonaphthofuran to a furonaphthopyran.

Original language	English
Pages (from-to)	1318-1322
Number of pages	5
Journal	Synlett
Issue number	8
DOIs	https://doi.org/10.1055/s-2002-32955
Publication status	Published - 2002
Externally published	Yes

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title = "Synthesis of azido analogues of medermycin",

abstract = "The synthesis of azido analogues 2a,2b of the pyrano-naphthoquinone antibiotic medermycin 1 has been achieved in eight steps from naphthol 8 and azido glycosyl sugar 7 in 9.3% overall yield. Key steps include the direct BF3·Et2O promoted C-glycosylation of naphthol 8, introduction of an acetyl group onto a bromonaphthoquinone via Stille coupling with (α-ethoxy-vinyl)tributyltin, furofuran annulation of a naphthoquinone to a furonaphthofuran using 2-trimethylsilyloxyfuran 5 and oxidative rearrangement of a furonaphthofuran to a furonaphthopyran.",

keywords = "Amino sugar, C-glycoside, Naphthoquinone, Pyranonaphthoquinone antibiotics, Stille coupling",

author = "Brimble, {Margaret A.} and Davey, {Roger M.} and McLeod, {Malcolm D.}",

year = "2002",

doi = "10.1055/s-2002-32955",

language = "English",

pages = "1318--1322",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "8",

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T1 - Synthesis of azido analogues of medermycin

AU - Brimble, Margaret A.

AU - Davey, Roger M.

AU - McLeod, Malcolm D.

PY - 2002

Y1 - 2002

N2 - The synthesis of azido analogues 2a,2b of the pyrano-naphthoquinone antibiotic medermycin 1 has been achieved in eight steps from naphthol 8 and azido glycosyl sugar 7 in 9.3% overall yield. Key steps include the direct BF3·Et2O promoted C-glycosylation of naphthol 8, introduction of an acetyl group onto a bromonaphthoquinone via Stille coupling with (α-ethoxy-vinyl)tributyltin, furofuran annulation of a naphthoquinone to a furonaphthofuran using 2-trimethylsilyloxyfuran 5 and oxidative rearrangement of a furonaphthofuran to a furonaphthopyran.

AB - The synthesis of azido analogues 2a,2b of the pyrano-naphthoquinone antibiotic medermycin 1 has been achieved in eight steps from naphthol 8 and azido glycosyl sugar 7 in 9.3% overall yield. Key steps include the direct BF3·Et2O promoted C-glycosylation of naphthol 8, introduction of an acetyl group onto a bromonaphthoquinone via Stille coupling with (α-ethoxy-vinyl)tributyltin, furofuran annulation of a naphthoquinone to a furonaphthofuran using 2-trimethylsilyloxyfuran 5 and oxidative rearrangement of a furonaphthofuran to a furonaphthopyran.

KW - Amino sugar

KW - C-glycoside

KW - Naphthoquinone

KW - Pyranonaphthoquinone antibiotics

KW - Stille coupling

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U2 - 10.1055/s-2002-32955

DO - 10.1055/s-2002-32955

M3 - Article

SN - 0936-5214

SP - 1318

EP - 1322

JO - Synlett

JF - Synlett

IS - 8

ER -

Synthesis of azido analogues of medermycin

Abstract

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