Total syntheses of the resorcylic acid lactones paecilomycin F and cochliomycin C using an intramolecular loh-type α-allylation reaction for macrolide formation

Xiang Ma; Benoit Bolte; Martin G. Banwell; Anthony C. Willis

doi:10.1021/acs.orglett.6b01963

Total syntheses of the resorcylic acid lactones paecilomycin F and cochliomycin C using an intramolecular loh-type α-allylation reaction for macrolide formation

Xiang Ma, Benoit Bolte, Martin G. Banwell^*, Anthony C. Willis

^*Corresponding author for this work

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

14 Citations (Scopus)

Abstract

Subjection of the resorcylic ester 16 to a Nozaki-Hiyama-Kishi reaction afforded the 12-membered lactone 17, while treatment of it under the Loh-type α-allylation conditions using indium metal gave the isomeric, 14-membered macrolide 18. Compound 18 was readily elaborated to the resorcylic acid lactone type natural products paecilomycin F and cochliomycin C.

Original language	English
Pages (from-to)	4226-4229
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.6b01963
Publication status	Published - 2 Sept 2016

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abstract = "Subjection of the resorcylic ester 16 to a Nozaki-Hiyama-Kishi reaction afforded the 12-membered lactone 17, while treatment of it under the Loh-type α-allylation conditions using indium metal gave the isomeric, 14-membered macrolide 18. Compound 18 was readily elaborated to the resorcylic acid lactone type natural products paecilomycin F and cochliomycin C.",

author = "Xiang Ma and Benoit Bolte and Banwell, {Martin G.} and Willis, {Anthony C.}",

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AU - Ma, Xiang

AU - Bolte, Benoit

AU - Banwell, Martin G.

AU - Willis, Anthony C.

PY - 2016/9/2

Y1 - 2016/9/2

N2 - Subjection of the resorcylic ester 16 to a Nozaki-Hiyama-Kishi reaction afforded the 12-membered lactone 17, while treatment of it under the Loh-type α-allylation conditions using indium metal gave the isomeric, 14-membered macrolide 18. Compound 18 was readily elaborated to the resorcylic acid lactone type natural products paecilomycin F and cochliomycin C.

AB - Subjection of the resorcylic ester 16 to a Nozaki-Hiyama-Kishi reaction afforded the 12-membered lactone 17, while treatment of it under the Loh-type α-allylation conditions using indium metal gave the isomeric, 14-membered macrolide 18. Compound 18 was readily elaborated to the resorcylic acid lactone type natural products paecilomycin F and cochliomycin C.

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U2 - 10.1021/acs.orglett.6b01963

DO - 10.1021/acs.orglett.6b01963

M3 - Article

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JF - Organic Letters

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ER -

Total syntheses of the resorcylic acid lactones paecilomycin F and cochliomycin C using an intramolecular loh-type α-allylation reaction for macrolide formation

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