Total Synthesis and Stereochemical Assignment of Myriaporones 1, 3, and 4

• Published in: Angewandte Chemie (International ed.) Vol. 43; no. 13; pp. 1728 - 1730
• Main Authors: Fleming, Kristen N., Taylor, Richard E.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 19.03.2004; WILEY‐VCH Verlag; Wiley
• Subjects: aldol reaction; Alkenes - chemical synthesis; Alkenes - chemistry; Chemistry; Chemistry, Multidisciplinary; diastereoselectivity; epoxidation; Epoxy Compounds - chemical synthesis; Epoxy Compounds - chemistry; Molecular Conformation; natural products; Physical Sciences; Pyrans - chemical synthesis; Pyrans - chemistry; Science & Technology; Stereoisomerism; total synthesis; aldol reaction; SECO-ACID; EFFICIENT MACROLACTONIZATION; diastereoselectivity; TEDANOLIDE; ALCOHOLS; natural products; DIVERGENT APPROACH; epoxidation; 18-MEMBERED ANTITUMOR MACROLIDE; FRAGMENT; INTERMEDIATE; total synthesis; STEREOSELECTIVE-SYNTHESIS

Two stereoselective aldol reactions, a nitrile oxide cycloaddition, and a stereoselective late‐stage epoxidation were key steps in the total synthesis of myriaporones 1, 3, and 4 (see scheme). The synthesis allowed the unambiguous assignment of stereogenic centers not previously assigned for these c...