Application of the Intramolecular Vinylogous Morita−Baylis−Hillman Reaction toward the Synthesis of the Spinosyn A Tricyclic Nucleus

• Published in: Organic letters Vol. 4; no. 18; pp. 3157 - 3160
• Main Authors: Mergott, Dustin J, Frank, Scott A, Roush, William R
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 05.09.2002; Amer Chemical Soc
• Subjects: Anti-Bacterial Agents - chemical synthesis; Chemistry; Chemistry, Organic; Cyclization; Insecticides - chemical synthesis; Macrolides; Physical Sciences; Saccharopolyspora - chemistry; Science & Technology; Stereoisomerism; Vinyl Compounds - chemistry; ALCOHOLS; CHEMISTRY; BOTTOM-HALF; ENANTIOSELECTIVE SYNTHESIS; STEREOCONTROL; CHLOROTHRICOLIDE

A concise synthesis of the spinosyn A tricyclic nucleus 27 has been developed by a route featuring a one-pot tandem intramolecular Diels−Alder reaction and intramolecular vinylogous Morita−Baylis−Hillman cyclization in which five stereocenters in tricycle 10 are set with excellent selectivity.