Oxidative Routes to the Heterocyclic Cores of Benzothiazole Natural Products

Christopher E. Blunt; Christopher C. Nawrat; Lucille Lebozec; Mantas Liutkus; Yang Liu; William Lewis; Christopher J. Moody

doi:10.1055/s-0035-1560722

Oxidative Routes to the Heterocyclic Cores of Benzothiazole Natural Products

Christopher E. Blunt, Christopher C. Nawrat, Lucille Lebozec, Mantas Liutkus, Yang Liu, William Lewis, Christopher J. Moody^*

^*Corresponding author for this work

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

10 Citations (Scopus)

Abstract

Methyl 6-(2-acetylaminoethyl)-4-hydroxy-benzothiazole-2-carboxylate, the benzothiazole core of the natural product violatinctamine, was prepared in a biomimetic oxidative route from N-acetyldopamine and cysteine methyl ester. In an alternative oxidative cyclization, ethyl 6-benzyloxy-5-methoxybenzo[d]thiazole-2-carboxylate, the heterocyclic core of erythrazole A, was also prepared.

Original language	English
Article number	st-2015-d0651-l
Pages (from-to)	37-40
Number of pages	4
Journal	Synlett
Volume	27
Issue number	1
DOIs	https://doi.org/10.1055/s-0035-1560722
Publication status	Published - 4 Jan 2016
Externally published	Yes

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title = "Oxidative Routes to the Heterocyclic Cores of Benzothiazole Natural Products",

abstract = "Methyl 6-(2-acetylaminoethyl)-4-hydroxy-benzothiazole-2-carboxylate, the benzothiazole core of the natural product violatinctamine, was prepared in a biomimetic oxidative route from N-acetyldopamine and cysteine methyl ester. In an alternative oxidative cyclization, ethyl 6-benzyloxy-5-methoxybenzo[d]thiazole-2-carboxylate, the heterocyclic core of erythrazole A, was also prepared.",

keywords = "amino acids, heterocycles, natural products, oxidation, quinones",

author = "Blunt, \{Christopher E.\} and Nawrat, \{Christopher C.\} and Lucille Lebozec and Mantas Liutkus and Yang Liu and William Lewis and Moody, \{Christopher J.\}",

note = "Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart New York Synlett 2016.",

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doi = "10.1055/s-0035-1560722",

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T1 - Oxidative Routes to the Heterocyclic Cores of Benzothiazole Natural Products

AU - Blunt, Christopher E.

AU - Nawrat, Christopher C.

AU - Lebozec, Lucille

AU - Liutkus, Mantas

AU - Liu, Yang

AU - Lewis, William

AU - Moody, Christopher J.

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart New York Synlett 2016.

PY - 2016/1/4

Y1 - 2016/1/4

N2 - Methyl 6-(2-acetylaminoethyl)-4-hydroxy-benzothiazole-2-carboxylate, the benzothiazole core of the natural product violatinctamine, was prepared in a biomimetic oxidative route from N-acetyldopamine and cysteine methyl ester. In an alternative oxidative cyclization, ethyl 6-benzyloxy-5-methoxybenzo[d]thiazole-2-carboxylate, the heterocyclic core of erythrazole A, was also prepared.

AB - Methyl 6-(2-acetylaminoethyl)-4-hydroxy-benzothiazole-2-carboxylate, the benzothiazole core of the natural product violatinctamine, was prepared in a biomimetic oxidative route from N-acetyldopamine and cysteine methyl ester. In an alternative oxidative cyclization, ethyl 6-benzyloxy-5-methoxybenzo[d]thiazole-2-carboxylate, the heterocyclic core of erythrazole A, was also prepared.

KW - amino acids

KW - heterocycles

KW - natural products

KW - oxidation

KW - quinones

UR - https://www.scopus.com/pages/publications/84950254670

U2 - 10.1055/s-0035-1560722

DO - 10.1055/s-0035-1560722

M3 - Article

SN - 0936-5214

VL - 27

SP - 37

EP - 40

JO - Synlett

JF - Synlett

IS - 1

M1 - st-2015-d0651-l

ER -

Oxidative Routes to the Heterocyclic Cores of Benzothiazole Natural Products

Abstract

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