Expedient total synthesis of pyrrothine natural products and analogs

Expedient total synthesis of pyrrothine natural products and analogs
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DOI:
10.1039/b616411k
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发表时间:
2007-01-01
影响因子:
3.2
通讯作者:
Nielsen, John
Nielsen, John
中科院分区:
化学3区
文献类型:
--
作者:
Hjelmgaard, Thomas;Givskov, Michael;Nielsen, John

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本文描述了两种pyrothine天然产物holomycin 1a(7步,总体11%)和xenorhabdin i1c(7步,总体11%)及其类似物通过一个共同的后期中间体的便利和直接的全合成。该途径通过盐酸吡虫氨酸中间体10进行(6步,总体17%),这也使得类似物的合成非常快速,如1f, 1g和1h的合成(7步,总体11 - 12%)。
This paper describes an expedient and straightforward total synthesis of the two pyrrothine natural products holomycin 1a ( 7 steps, 11% overall) and xenorhabdin I 1c ( 7 steps, 11% overall) and analogs thereof via a common late-stage intermediate. The pathway proceeds via the pyrrothine hydrochloride intermediate 10 ( 6 steps, 17% overall) which also gave access to very fast synthesis of analogs as demonstrated by the synthesis of 1f, 1g and 1h ( 7 steps, 11 - 12% overall).