Synthesis and reactivity of a putative biogenetic precursor to tricholomenyns B, C, D and E

Xinghua Ma; Jasmine C. Jury; Martin G. Banwell

doi:10.1016/j.tetlet.2010.11.139

Synthesis and reactivity of a putative biogenetic precursor to tricholomenyns B, C, D and E

Xinghua Ma, Jasmine C. Jury, Martin G. Banwell

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11 Citations (Scopus)

Abstract

A chemoenzymatic synthesis of the putative biogenetic precursor, 6, to the epoxy-quinol type natural products, tricholomenyns B, C, D and E (2-5, respectively), has been achieved. However, treatment of compound 6 under a variety of conditions failed to effect its conversion into any of the natural products 2-5. In contrast, the simple model system 22 reacts with acetic acid in the presence of stoichiometric quantities of Ti(OPr-i)₄ to give the diacetate 23.

Original language	English
Pages (from-to)	2192-2194
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	17
DOIs	https://doi.org/10.1016/j.tetlet.2010.11.139
Publication status	Published - 27 Apr 2011

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10.1016/j.tetlet.2010.11.139

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title = "Synthesis and reactivity of a putative biogenetic precursor to tricholomenyns B, C, D and E",

abstract = "A chemoenzymatic synthesis of the putative biogenetic precursor, 6, to the epoxy-quinol type natural products, tricholomenyns B, C, D and E (2-5, respectively), has been achieved. However, treatment of compound 6 under a variety of conditions failed to effect its conversion into any of the natural products 2-5. In contrast, the simple model system 22 reacts with acetic acid in the presence of stoichiometric quantities of Ti(OPr-i)4 to give the diacetate 23.",

keywords = "Chemoenzymatic, Epoxy-quinol, Sonogashira reaction, Synthesis, Tricholomenyns",

author = "Xinghua Ma and Jury, {Jasmine C.} and Banwell, {Martin G.}",

year = "2011",

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T1 - Synthesis and reactivity of a putative biogenetic precursor to tricholomenyns B, C, D and E

AU - Ma, Xinghua

AU - Jury, Jasmine C.

AU - Banwell, Martin G.

PY - 2011/4/27

Y1 - 2011/4/27

N2 - A chemoenzymatic synthesis of the putative biogenetic precursor, 6, to the epoxy-quinol type natural products, tricholomenyns B, C, D and E (2-5, respectively), has been achieved. However, treatment of compound 6 under a variety of conditions failed to effect its conversion into any of the natural products 2-5. In contrast, the simple model system 22 reacts with acetic acid in the presence of stoichiometric quantities of Ti(OPr-i)4 to give the diacetate 23.

AB - A chemoenzymatic synthesis of the putative biogenetic precursor, 6, to the epoxy-quinol type natural products, tricholomenyns B, C, D and E (2-5, respectively), has been achieved. However, treatment of compound 6 under a variety of conditions failed to effect its conversion into any of the natural products 2-5. In contrast, the simple model system 22 reacts with acetic acid in the presence of stoichiometric quantities of Ti(OPr-i)4 to give the diacetate 23.

KW - Chemoenzymatic

KW - Epoxy-quinol

KW - Sonogashira reaction

KW - Synthesis

KW - Tricholomenyns

UR - http://www.scopus.com/inward/record.url?scp=79953190721&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2010.11.139

DO - 10.1016/j.tetlet.2010.11.139

M3 - Article

SN - 0040-4039

VL - 52

SP - 2192

EP - 2194

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 17

ER -

Synthesis and reactivity of a putative biogenetic precursor to tricholomenyns B, C, D and E

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