Exploring prins strategies for the synthesis of okilactomycin

Jason M. Tenenbaum; William J. Morris; Daniel W. Custar; Karl A. Scheidt

doi:10.1016/B978-0-08-099362-1.00008-4

Exploring prins strategies for the synthesis of okilactomycin

Jason M. Tenenbaum, William J. Morris, Daniel W. Custar, Karl A. Scheidt^*

^*Corresponding author for this work

Chemistry

Research output: Chapter in Book/Report/Conference proceeding › Chapter

1 Scopus citations

Abstract

This account describes the convergent synthesis of (-)-okilactomycin. The first-generation approach focused on the assembly of two complex fragments through a Prins reaction of a dioxinone and α-hydroxy aldehyde. While this route was not ultimately successful, a related Maitland-Japp process employing a β-keto ester in place of the dioxinone fragment provided the necessary union of functionalized intermediate, thereby establishing the full carbon framework of the natural product. The synthesis also employed a highly diastereoselective Lewis acid-promoted Diels-Alder reaction and an olefin ring-closing metathesis to close the strained 11-membered macrocycle of the natural product.

Original language	English (US)
Title of host publication	Strategies and Tactics in Organic Synthesis
Publisher	Academic Press Inc
Pages	231-248
Number of pages	18
ISBN (Print)	9780080993621
DOIs	https://doi.org/10.1016/B978-0-08-099362-1.00008-4
State	Published - 2013

Publication series

Name	Strategies and Tactics in Organic Synthesis
Volume	9
ISSN (Print)	1874-6004

Funding

Financial support for this work has been provided by the NCI (R01 CA126827), the American Cancer Society (Research Scholar Grant), the Elsa U. Pardee Foundation, Amgen, and GlaxoSmithKline. W. J. M. thanks Abbott Laboratories for a graduate fellowship. We thank Astellas Pharma for spectral data of natural (+)-okilactomycin.

ASJC Scopus subject areas

Drug Discovery
Organic Chemistry

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10.1016/B978-0-08-099362-1.00008-4

Cite this

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title = "Exploring prins strategies for the synthesis of okilactomycin",

abstract = "This account describes the convergent synthesis of (-)-okilactomycin. The first-generation approach focused on the assembly of two complex fragments through a Prins reaction of a dioxinone and α-hydroxy aldehyde. While this route was not ultimately successful, a related Maitland-Japp process employing a β-keto ester in place of the dioxinone fragment provided the necessary union of functionalized intermediate, thereby establishing the full carbon framework of the natural product. The synthesis also employed a highly diastereoselective Lewis acid-promoted Diels-Alder reaction and an olefin ring-closing metathesis to close the strained 11-membered macrocycle of the natural product.",

author = "Tenenbaum, {Jason M.} and Morris, {William J.} and Custar, {Daniel W.} and Scheidt, {Karl A.}",

note = "Funding Information: Financial support for this work has been provided by the NCI (R01 CA126827), the American Cancer Society (Research Scholar Grant), the Elsa U. Pardee Foundation, Amgen, and GlaxoSmithKline. W. J. M. thanks Abbott Laboratories for a graduate fellowship. We thank Astellas Pharma for spectral data of natural (+)-okilactomycin.",

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AU - Custar, Daniel W.

AU - Scheidt, Karl A.

N1 - Funding Information: Financial support for this work has been provided by the NCI (R01 CA126827), the American Cancer Society (Research Scholar Grant), the Elsa U. Pardee Foundation, Amgen, and GlaxoSmithKline. W. J. M. thanks Abbott Laboratories for a graduate fellowship. We thank Astellas Pharma for spectral data of natural (+)-okilactomycin.

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AB - This account describes the convergent synthesis of (-)-okilactomycin. The first-generation approach focused on the assembly of two complex fragments through a Prins reaction of a dioxinone and α-hydroxy aldehyde. While this route was not ultimately successful, a related Maitland-Japp process employing a β-keto ester in place of the dioxinone fragment provided the necessary union of functionalized intermediate, thereby establishing the full carbon framework of the natural product. The synthesis also employed a highly diastereoselective Lewis acid-promoted Diels-Alder reaction and an olefin ring-closing metathesis to close the strained 11-membered macrocycle of the natural product.

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Exploring prins strategies for the synthesis of okilactomycin

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