Modular Total Syntheses of the Marine-Derived Resorcylic Acid Lactones Cochliomycins A and B Using a Late-Stage Nozaki-Hiyama-Kishi Macrocyclization Reaction

Benoit Bolte; Jose A. Basutto; Christopher S. Bryan; Mary J. Garson; Martin G. Banwell; Jas S. Ward

doi:10.1021/jo5024602

Modular Total Syntheses of the Marine-Derived Resorcylic Acid Lactones Cochliomycins A and B Using a Late-Stage Nozaki-Hiyama-Kishi Macrocyclization Reaction

Benoit Bolte, Jose A. Basutto, Christopher S. Bryan, Mary J. Garson, Martin G. Banwell^*, Jas S. Ward

^*Corresponding author for this work

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

30 Citations (Scopus)

Abstract

The natural products cochliomycin A (1) and cochliomycin B (2), two resorcylic acid lactones obtained from marine sources, have been prepared in a concise and stereocontrolled manner from the readily accessible building blocks 4-6. Olefin cross-metathesis, trans-esterification and Nozaki-Hiyama-Kishi (NHK) macrocyclization reactions were employed in the key steps. Hydrolysis of the immediate precursor to cochliomycin B affords the resorcylic acid lactone zeaenol (24).

Original language	English
Pages (from-to)	460-470
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	80
Issue number	1
DOIs	https://doi.org/10.1021/jo5024602
Publication status	Published - 2 Jan 2015

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title = "Modular Total Syntheses of the Marine-Derived Resorcylic Acid Lactones Cochliomycins A and B Using a Late-Stage Nozaki-Hiyama-Kishi Macrocyclization Reaction",

abstract = "The natural products cochliomycin A (1) and cochliomycin B (2), two resorcylic acid lactones obtained from marine sources, have been prepared in a concise and stereocontrolled manner from the readily accessible building blocks 4-6. Olefin cross-metathesis, trans-esterification and Nozaki-Hiyama-Kishi (NHK) macrocyclization reactions were employed in the key steps. Hydrolysis of the immediate precursor to cochliomycin B affords the resorcylic acid lactone zeaenol (24).",

author = "Benoit Bolte and Basutto, \{Jose A.\} and Bryan, \{Christopher S.\} and Garson, \{Mary J.\} and Banwell, \{Martin G.\} and Ward, \{Jas S.\}",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2015",

month = jan,

day = "2",

doi = "10.1021/jo5024602",

language = "English",

volume = "80",

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journal = "Journal of Organic Chemistry",

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T1 - Modular Total Syntheses of the Marine-Derived Resorcylic Acid Lactones Cochliomycins A and B Using a Late-Stage Nozaki-Hiyama-Kishi Macrocyclization Reaction

AU - Bolte, Benoit

AU - Basutto, Jose A.

AU - Bryan, Christopher S.

AU - Garson, Mary J.

AU - Banwell, Martin G.

AU - Ward, Jas S.

PY - 2015/1/2

Y1 - 2015/1/2

N2 - The natural products cochliomycin A (1) and cochliomycin B (2), two resorcylic acid lactones obtained from marine sources, have been prepared in a concise and stereocontrolled manner from the readily accessible building blocks 4-6. Olefin cross-metathesis, trans-esterification and Nozaki-Hiyama-Kishi (NHK) macrocyclization reactions were employed in the key steps. Hydrolysis of the immediate precursor to cochliomycin B affords the resorcylic acid lactone zeaenol (24).

AB - The natural products cochliomycin A (1) and cochliomycin B (2), two resorcylic acid lactones obtained from marine sources, have been prepared in a concise and stereocontrolled manner from the readily accessible building blocks 4-6. Olefin cross-metathesis, trans-esterification and Nozaki-Hiyama-Kishi (NHK) macrocyclization reactions were employed in the key steps. Hydrolysis of the immediate precursor to cochliomycin B affords the resorcylic acid lactone zeaenol (24).

UR - https://www.scopus.com/pages/publications/84928881167

U2 - 10.1021/jo5024602

DO - 10.1021/jo5024602

M3 - Article

SN - 0022-3263

VL - 80

SP - 460

EP - 470

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 1

ER -

Modular Total Syntheses of the Marine-Derived Resorcylic Acid Lactones Cochliomycins A and B Using a Late-Stage Nozaki-Hiyama-Kishi Macrocyclization Reaction

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