Total Synthesis of Suillusin

Meng Yao Zhang; Lara R. Malins; Jas S. Ward; Russell A. Barrow

doi:10.1021/acs.orglett.8b03234

Total Synthesis of Suillusin

Meng Yao Zhang^*, Lara R. Malins, Jas S. Ward, Russell A. Barrow

^*Corresponding author for this work

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

2 Citations (Scopus)

Abstract

The first total synthesis of the fungal natural product suillusin is reported. The key features of the synthesis include a Michael-benzoin multicatalytic cascade that assembles the entire carbon framework in a single step, and a Rubottom-Swern oxidation sequence that yields the requisite diketone oxidation state of the core framework. This 10-step synthesis of suillusin will allow further evaluation of the biogenesis and the biological activity of the fungal metabolite.

Original language	English
Pages (from-to)	7304-7307
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.8b03234
Publication status	Published - 16 Nov 2018

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title = "Total Synthesis of Suillusin",

abstract = "The first total synthesis of the fungal natural product suillusin is reported. The key features of the synthesis include a Michael-benzoin multicatalytic cascade that assembles the entire carbon framework in a single step, and a Rubottom-Swern oxidation sequence that yields the requisite diketone oxidation state of the core framework. This 10-step synthesis of suillusin will allow further evaluation of the biogenesis and the biological activity of the fungal metabolite.",

author = "Zhang, {Meng Yao} and Malins, {Lara R.} and Ward, {Jas S.} and Barrow, {Russell A.}",

note = "Publisher Copyright: Copyright {\textcopyright} 2018 American Chemical Society.",

year = "2018",

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day = "16",

doi = "10.1021/acs.orglett.8b03234",

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AU - Zhang, Meng Yao

AU - Malins, Lara R.

AU - Ward, Jas S.

AU - Barrow, Russell A.

PY - 2018/11/16

Y1 - 2018/11/16

N2 - The first total synthesis of the fungal natural product suillusin is reported. The key features of the synthesis include a Michael-benzoin multicatalytic cascade that assembles the entire carbon framework in a single step, and a Rubottom-Swern oxidation sequence that yields the requisite diketone oxidation state of the core framework. This 10-step synthesis of suillusin will allow further evaluation of the biogenesis and the biological activity of the fungal metabolite.

AB - The first total synthesis of the fungal natural product suillusin is reported. The key features of the synthesis include a Michael-benzoin multicatalytic cascade that assembles the entire carbon framework in a single step, and a Rubottom-Swern oxidation sequence that yields the requisite diketone oxidation state of the core framework. This 10-step synthesis of suillusin will allow further evaluation of the biogenesis and the biological activity of the fungal metabolite.

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DO - 10.1021/acs.orglett.8b03234

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SN - 1523-7060

VL - 20

SP - 7304

EP - 7307

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

Total Synthesis of Suillusin

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