α-Ketol Rearrangement for Accessing Tetracyclic Natural Products

Alexandru Sara; Ulrike Eggert; Markus Kalesse

doi:10.1021/acs.orglett.5c02235

α-Ketol Rearrangement for Accessing Tetracyclic Natural Products

Alexandru Sara
, Ulrike Eggert
, Markus Kalesse

Institute of Organic Chemistry

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

Abstract

Tetracyclic natural products, which utilize the tetracycline skeleton, demonstrate a diverse array of biological activities. A critical structural feature of these compounds is the tertiary alcohol situated within a cis-decalin framework. In this study, we present a comprehensive protocol for the synthesis of tricyclic building blocks and complete carbon frameworks. This methodology facilitates the stereoselective synthesis of a specific enantiomer as well as its inversion to the corresponding opposite isomer via a ketol rearrangement.

Original language	English
Pages (from-to)	8154-8157
Number of pages	4
Journal	Organic letters
Volume	27
Issue number	30
E-pub ahead of print	22 Jul 2025
DOIs	https://doi.org/10.1021/acs.orglett.5c02235
Publication status	Published - 1 Aug 2025

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.5c02235Licence: CC BY 4.0

Cite this

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abstract = "Tetracyclic natural products, which utilize the tetracycline skeleton, demonstrate a diverse array of biological activities. A critical structural feature of these compounds is the tertiary alcohol situated within a cis-decalin framework. In this study, we present a comprehensive protocol for the synthesis of tricyclic building blocks and complete carbon frameworks. This methodology facilitates the stereoselective synthesis of a specific enantiomer as well as its inversion to the corresponding opposite isomer via a ketol rearrangement.",

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AB - Tetracyclic natural products, which utilize the tetracycline skeleton, demonstrate a diverse array of biological activities. A critical structural feature of these compounds is the tertiary alcohol situated within a cis-decalin framework. In this study, we present a comprehensive protocol for the synthesis of tricyclic building blocks and complete carbon frameworks. This methodology facilitates the stereoselective synthesis of a specific enantiomer as well as its inversion to the corresponding opposite isomer via a ketol rearrangement.

UR - https://www.scopus.com/pages/publications/105012852507

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α-Ketol Rearrangement for Accessing Tetracyclic Natural Products

Abstract

ASJC Scopus subject areas

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