A Stereocontrolled Annulation of the Taccalonolide Epoxy Lactone onto the Molecular Framework of trans-Androsterone

Jakob Danielsson; Diana X. Sun; Xiao Yang Chen; April L. Risinger; Susan L. Mooberry; Erik J. Sorensen

doi:10.1021/acs.orglett.7b02349

A Stereocontrolled Annulation of the Taccalonolide Epoxy Lactone onto the Molecular Framework of trans-Androsterone

Jakob Danielsson, Diana X. Sun, Xiao Yang Chen, April L. Risinger, Susan L. Mooberry, Erik J. Sorensen

Chemistry

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

8 Scopus citations

Abstract

A robust and scalable route to the taccalonolide skeleton starting from trans-androsterone is presented. The synthesis features a cyclic hydroboration carbonylation reaction, which effectively establishes the trans-hydrindane DE ring junction in a remarkable annulation reaction, as well as a Claisen rearrangement and a catalytic Ullmann-type cyclization. This work is part of a larger effort to uncover new clinical candidates from the taccalonolide class of anticancer agents through advances in chemical synthesis.

Original language	English (US)
Pages (from-to)	4892-4895
Number of pages	4
Journal	Organic letters
Volume	19
Issue number	18
DOIs	https://doi.org/10.1021/acs.orglett.7b02349
State	Published - Sep 15 2017

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.7b02349

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abstract = "A robust and scalable route to the taccalonolide skeleton starting from trans-androsterone is presented. The synthesis features a cyclic hydroboration carbonylation reaction, which effectively establishes the trans-hydrindane DE ring junction in a remarkable annulation reaction, as well as a Claisen rearrangement and a catalytic Ullmann-type cyclization. This work is part of a larger effort to uncover new clinical candidates from the taccalonolide class of anticancer agents through advances in chemical synthesis.",

author = "Jakob Danielsson and Sun, \{Diana X.\} and Chen, \{Xiao Yang\} and Risinger, \{April L.\} and Mooberry, \{Susan L.\} and Sorensen, \{Erik J.\}",

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AU - Danielsson, Jakob

AU - Sun, Diana X.

AU - Chen, Xiao Yang

AU - Risinger, April L.

AU - Mooberry, Susan L.

AU - Sorensen, Erik J.

PY - 2017/9/15

Y1 - 2017/9/15

N2 - A robust and scalable route to the taccalonolide skeleton starting from trans-androsterone is presented. The synthesis features a cyclic hydroboration carbonylation reaction, which effectively establishes the trans-hydrindane DE ring junction in a remarkable annulation reaction, as well as a Claisen rearrangement and a catalytic Ullmann-type cyclization. This work is part of a larger effort to uncover new clinical candidates from the taccalonolide class of anticancer agents through advances in chemical synthesis.

AB - A robust and scalable route to the taccalonolide skeleton starting from trans-androsterone is presented. The synthesis features a cyclic hydroboration carbonylation reaction, which effectively establishes the trans-hydrindane DE ring junction in a remarkable annulation reaction, as well as a Claisen rearrangement and a catalytic Ullmann-type cyclization. This work is part of a larger effort to uncover new clinical candidates from the taccalonolide class of anticancer agents through advances in chemical synthesis.

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A Stereocontrolled Annulation of the Taccalonolide Epoxy Lactone onto the Molecular Framework of trans-Androsterone

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