The total synthesis of the diepoxycyclohexanone antibiotic aranorosin and novel synthetic analogues

A  McKillop; L  McLaren; R J K  Taylor; R J  Watson; N J  Lewis

The total synthesis of the diepoxycyclohexanone antibiotic aranorosin and novel synthetic analogues

A McKillop, L McLaren, R J K Taylor, R J Watson, N J Lewis

Chemistry

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

Abstract

A short synthesis of the novel antibiotic aranorosin in chiral form is described which employs (i) a novel hypervalent iodine-mediated oxidative hydroxylation of a tyrosinal derivative and (ii) a stereocontrolled cis-bisepoxidation in the key steps. A similar procedure was employed to prepare 6'-epiaranorosin, and hence establish the stereochemistry of the natural compound, and to prepare novel aranorosin analogues. An organometallic route is described which gives desamidoaranorosin.

Original language	English
Pages (from-to)	1385-1393
Number of pages	9
Journal	Journal of the Chemical Society-Perkin Transactions 1
Issue number	12
Publication status	Published - 21 Jun 1996

Keywords

HYPERVALENT IODINE OXIDATION
PSEUDOARACHNIOTUS-ROSEUS
N-ACYLOXAZOLIDINONES
CONVENIENT METHOD
MONOACETALS
EPOXIDES
NUCLEUS
ETHERS
ALPHA
ACIDS

Cite this

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title = "The total synthesis of the diepoxycyclohexanone antibiotic aranorosin and novel synthetic analogues",

abstract = "A short synthesis of the novel antibiotic aranorosin in chiral form is described which employs (i) a novel hypervalent iodine-mediated oxidative hydroxylation of a tyrosinal derivative and (ii) a stereocontrolled cis-bisepoxidation in the key steps. A similar procedure was employed to prepare 6'-epiaranorosin, and hence establish the stereochemistry of the natural compound, and to prepare novel aranorosin analogues. An organometallic route is described which gives desamidoaranorosin.",

keywords = "HYPERVALENT IODINE OXIDATION, PSEUDOARACHNIOTUS-ROSEUS, N-ACYLOXAZOLIDINONES, CONVENIENT METHOD, MONOACETALS, EPOXIDES, NUCLEUS, ETHERS, ALPHA, ACIDS",

author = "A McKillop and L McLaren and Taylor, {R J K} and Watson, {R J} and Lewis, {N J}",

year = "1996",

month = jun,

day = "21",

language = "English",

pages = "1385--1393",

journal = "Journal of the Chemical Society-Perkin Transactions 1",

issn = "0300-922X",

publisher = "Chemical Society",

number = "12",

}

TY - JOUR

T1 - The total synthesis of the diepoxycyclohexanone antibiotic aranorosin and novel synthetic analogues

AU - McKillop, A

AU - McLaren, L

AU - Taylor, R J K

AU - Watson, R J

AU - Lewis, N J

PY - 1996/6/21

Y1 - 1996/6/21

N2 - A short synthesis of the novel antibiotic aranorosin in chiral form is described which employs (i) a novel hypervalent iodine-mediated oxidative hydroxylation of a tyrosinal derivative and (ii) a stereocontrolled cis-bisepoxidation in the key steps. A similar procedure was employed to prepare 6'-epiaranorosin, and hence establish the stereochemistry of the natural compound, and to prepare novel aranorosin analogues. An organometallic route is described which gives desamidoaranorosin.

AB - A short synthesis of the novel antibiotic aranorosin in chiral form is described which employs (i) a novel hypervalent iodine-mediated oxidative hydroxylation of a tyrosinal derivative and (ii) a stereocontrolled cis-bisepoxidation in the key steps. A similar procedure was employed to prepare 6'-epiaranorosin, and hence establish the stereochemistry of the natural compound, and to prepare novel aranorosin analogues. An organometallic route is described which gives desamidoaranorosin.

KW - HYPERVALENT IODINE OXIDATION

KW - PSEUDOARACHNIOTUS-ROSEUS

KW - N-ACYLOXAZOLIDINONES

KW - CONVENIENT METHOD

KW - MONOACETALS

KW - EPOXIDES

KW - NUCLEUS

KW - ETHERS

KW - ALPHA

KW - ACIDS

M3 - Article

SN - 0300-922X

SP - 1385

EP - 1393

JO - Journal of the Chemical Society-Perkin Transactions 1

JF - Journal of the Chemical Society-Perkin Transactions 1

IS - 12

ER -