Enantioselective Total Synthesis of 3β‐Hydroxy‐7β‐kemp‐8(9)‐en‐6‐one, a Diterpene Isolated from Higher Termites. Issue 50 (15th November 2017)

• Record Type: Journal Article
• Authors: Wang, Yuzhou; Jäger, Anne; Gruner, Margit; Lübken, Tilo; Metz, Peter
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 50(2017)
• Page Start: 15861
• Page End: 15865
• Publication Date: 2017-11-15
• Subjects: domino reactions -- metathesis -- natural products -- sulfa-Michael addition -- vinyl epoxides; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201708561
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : Sulfur helps ! 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.