Enantioselective Total Synthesis of 3β-Hydroxy-7β-kemp-8(9)-en-6-one, a Diterpene Isolated from Higher Termites

Yuzhou Wang; Anne Jäger; Margit Gruner; Tilo Lübken; Peter Metz

doi:10.1002/anie.201708561

Enantioselective Total Synthesis of 3β-Hydroxy-7β-kemp-8(9)-en-6-one, a Diterpene Isolated from Higher Termites

Angew Chem Int Ed Engl. 2017 Dec 11;56(50):15861-15865. doi: 10.1002/anie.201708561. Epub 2017 Nov 15.

Authors

Yuzhou Wang¹, Anne Jäger¹, Margit Gruner¹, Tilo Lübken¹, Peter Metz¹

Affiliation

¹ Fachrichtung Chemie und Lebensmittelchemie, Organische Chemie I, Technische Universität Dresden, Bergstrasse 66, 01069, Dresden, Germany.

PMID: 28960721
DOI: 10.1002/anie.201708561

Abstract

The first total synthesis of the title diterpene was accomplished starting from the Wieland-Miescher ketone. A diastereoselective sulfa-Michael addition enabled the generation of the delicate β,γ-unsaturated ketone moiety, while the tetracyclic kempane skeleton was readily constructed through domino metathesis.

Keywords: domino reactions; metathesis; natural products; sulfa-Michael addition; vinyl epoxides.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Diterpenes / chemical synthesis*
Diterpenes / chemistry
Diterpenes / isolation & purification*
Isoptera / chemistry*
Molecular Conformation
Stereoisomerism

Substances

Diterpenes