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A total synthesis of spiruchostatin A

A total synthesis of spiruchostatin A
A total synthesis of spiruchostatin A
We achieved the total synthesis of the histone deacetylase inhibitor spiruchostatin A, as the prelude to the preparation of a combinatorial library of its analogues. Two key reactions were an asymmetric acetate aldol reaction using a Zr-enolate and macrolactonization Using the Shiina method.
spiruchostatin, cyclic depsipeptide, natural product synthesis, asymmetric aldol reaction 2-methyl-6-nitrobenzoic anhydride, chiral auxiliaries, depsipeptide, macrolactonization, condensations, lactonization, enolate, acids
0040-4039
1177-1180
Doi, Takayuki
b60ed49a-9d6f-450a-8d52-5d7bd7c6b012
Iijima, Yusuke
aa515bbc-66b6-4124-be4c-43dc9a9fff03
Shin-ya, Kazuo
34afd4d2-bf56-4da3-806b-58bab83fd700
Ganesan, A.
62aa5a87-9308-4383-8686-99726b6bcfb9
Takahashi, Takahashi
db1c63d1-c951-4e99-91f7-6ca94248dd88
Doi, Takayuki
b60ed49a-9d6f-450a-8d52-5d7bd7c6b012
Iijima, Yusuke
aa515bbc-66b6-4124-be4c-43dc9a9fff03
Shin-ya, Kazuo
34afd4d2-bf56-4da3-806b-58bab83fd700
Ganesan, A.
62aa5a87-9308-4383-8686-99726b6bcfb9
Takahashi, Takahashi
db1c63d1-c951-4e99-91f7-6ca94248dd88

Doi, Takayuki, Iijima, Yusuke, Shin-ya, Kazuo, Ganesan, A. and Takahashi, Takahashi (2006) A total synthesis of spiruchostatin A. Tetrahedron Letters, 47 (7), 1177-1180. (doi:10.1016/j.tetlet.2005.12.031).

Record type: Article

Abstract

We achieved the total synthesis of the histone deacetylase inhibitor spiruchostatin A, as the prelude to the preparation of a combinatorial library of its analogues. Two key reactions were an asymmetric acetate aldol reaction using a Zr-enolate and macrolactonization Using the Shiina method.

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More information

Published date: 2006
Keywords: spiruchostatin, cyclic depsipeptide, natural product synthesis, asymmetric aldol reaction 2-methyl-6-nitrobenzoic anhydride, chiral auxiliaries, depsipeptide, macrolactonization, condensations, lactonization, enolate, acids

Identifiers

Local EPrints ID: 44423
URI: http://eprints.soton.ac.uk/id/eprint/44423
ISSN: 0040-4039
PURE UUID: eaf8e89a-21a7-4a70-9bfd-1a38f642f18a

Catalogue record

Date deposited: 28 Feb 2007
Last modified: 13 Mar 2019 21:07

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