Studies on the Synthesis of Myriaporones : Stereoselective Synthesis of the C5-C13 Fragment Starting from D-Glucose via Regioselective Reductive Opening of Methoxybenzylidene Acetal

• Published in: Chemical & pharmaceutical bulletin Vol. 48; no. 11; pp. 1761 - 1765
• Main Authors: ZHENG, Bao-Zhong, YAMAUCHI, Megumi, DEI, Hiroo, YONEMITSU, Osamu
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 01.11.2000; Pharmaceutical Soc Japan; Maruzen
• Subjects: Aliphatic compounds; benzylidene acetal; Benzylidene Compounds - chemistry; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Epoxy Compounds - chemical synthesis; Exact sciences and technology; Glucose; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; marine product; Marine Toxins - chemical synthesis; Organic chemistry; Oxidation-Reduction; Pharmacology & Pharmacy; Physical Sciences; Preparations and properties; protecting group; Science & Technology; Spectrometry, Mass, Fast Atom Bombardment; Stereoisomerism; stereoselective synthesis; CONVERSION; TEDANOLIDE; benzylidene acetal; marine product; C1-C7 FRAGMENT; ALCOHOLS; KETONES; 18-MEMBERED ANTITUMOR MACROLIDE; EFFICIENT SHARPLESS DIHYDROXYLATION; stereoselective synthesis; C-13-C23 PART; AIDED CONFORMATIONAL DESIGN; protecting group; Chemical reduction; Stereoselectivity; Acetal; Protecting group; Regioselectivity; Aliphatic compound; Ketol; Glucose; Chemical synthesis; Acylate; Enone; Scission
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.48.1761

A stereoselective synthesis is described of the C5-C13 fragment (4) of myriaporone 4 (1) starting from D-glucose by a coupling of the C5-C9 aldehyde (5), prepared using a regioselective reductive ring-opening of methoxy-benzylidene acetal, with the C10-C13 iodoolefin (6).