Total Synthesis of Mycalolides A and B through Olefin Metathesis. Issue 47 (9th October 2015)

• Record Type: Journal Article
• Authors: Kita, Masaki; Oka, Hirotaka; Usui, Akihiro; Ishitsuka, Tomoya; Mogi, Yuzo; Watanabe, Hidekazu; Tsunoda, Masaki; Kigoshi, Hideo
• Is Part Of: Angewandte Chemie international edition. Volume 54:Issue 47(2015)
• Page Start: 14174
• Page End: 14178
• Publication Date: 2015-10-09
• Subjects: esterification -- macrolactonization -- natural products -- olefin metathesis -- total synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201507795
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: An asymmetric total synthesis of the trisoxazole marine macrolides mycalolides A and B is described. This synthesis involves the convergent assembly of highly functionalized C1–C19 trisoxazole and C20–C35 side‐chain segments through the use of olefin metathesis and esterification as well as Julia–Kocienski olefination and enamide formation as key steps. Abstract : From start to finish : An asymmetric total synthesis of the trisoxazole macrolides, mycalolides A and B, is described. The synthesis involves the convergent assembly of C1–C19 trisoxazole and C20–C35 side‐chain segments using olefin metathesis and esterification as key steps.