Skeletal Diversification via Heteroatom Linkage Control: Preparation of Bicyclic and Spirocyclic Scaffolds from NSubstituted Homopropargyl Alcohols

Painter, Thomas O.; Bunn, Jonathon R.; Schoenen, Frank J.; Douglas, Justin T.; Day, Victor W.; Santini, Conrad

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Issue Date

2013-04-13

Author

Painter, Thomas O.

Bunn, Jonathon R.

Schoenen, Frank J.

Douglas, Justin T.

Day, Victor W.

Santini, Conrad

Publisher

American Chemical Society

Type

Article

Article Version

Scholarly/refereed, author accepted manuscript

Rights

This document is the Accepted Manuscript version of a Published Work that appeared in final form in the Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/jo400077m.

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Abstract

The discovery and application of a new branching pathway synthesis strategy that rapidly produces skeletally diverse scaffolds is described. Two different scaffold types, one a bicyclic iodo-vinylidene tertiary amine/tertiary alcohol and the other, a spirocyclic 3-furanone, are each obtained using a two-step sequence featuring a common first step. Both scaffold types lead to intermediates that can be orthogonally diversified using the same final components. One of the scaffold types was obtained in sufficiently high yield that it was immediately used to produce a 97-compound library.

Citation

Painter, T. O., Bunn, J. R., Schoenen, F. J., Douglas, J. T., Day, V. W., & Santini, C. (2013). Skeletal Diversification via Heteroatom Linkage Control: Preparation of Bicyclic and Spirocyclic Scaffolds from N-Substituted Homopropargyl Alcohols. The Journal of Organic Chemistry, 78(8), 3720–3730. http://doi.org/10.1021/jo400077m

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